(R)-4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
- CAS No.
- 364077-84-9
- Chemical Name:
- (R)-4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
- Synonyms
- (R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid;BOC-D-PRO(4-OXO);Boc-4-0xo-D-Pro-OH;Boc-4-Oxo-D-Proline;Boc-4-Keto-D-Proline;N-BOC-4-OXO-D-PROLINE;(2R)-N-Boc-4-oxo-proline;(2R)-N-Boc-4-oxo-D-proline;N-Boc-4-oxo-D-proline Methyl ester;(R)-1-Boc-4-oxopyrrolidine-2-carboxylic acid
- CBNumber:
- CB4452407
- Molecular Formula:
- C10H15NO5
- Molecular Weight:
- 229.23
- MDL Number:
- MFCD06409980
- MOL File:
- 364077-84-9.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Boiling point | 390.8±42.0 °C(Predicted) |
|---|---|
| Density | 1.304±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| pka | 3.85±0.20(Predicted) |
| Appearance | white to off-white solid |
| InChI | InChI=1S/C10H15NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h7H,4-5H2,1-3H3,(H,13,14)/t7-/m1/s1 |
| InChIKey | CKYGSXRXTIKGAJ-SSDOTTSWSA-N |
| SMILES | N1(C(OC(C)(C)C)=O)CC(=O)C[C@@H]1C(O)=O |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319-H335 |
| Precautionary statements | P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501 |
(R)-4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester price More Price(35)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Biosynth | PPA07784 | (R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid | 364077-84-9 | 10g | $472 | 2026-06-04 | Buy |
| Biosynth | PPA07784 | (R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid | 364077-84-9 | 100g | $3540 | 2026-06-04 | Buy |
| Synthonix | B23298 | (R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid 97% | 364077-84-9 | 100mg | $18 | 2026-05-06 | Buy |
| Synthonix | B23298 | (R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid 97% | 364077-84-9 | 250mg | $20 | 2026-05-06 | Buy |
| Synthonix | B23298 | (R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid 97% | 364077-84-9 | 1g | $30 | 2026-05-06 | Buy |
(R)-4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester Chemical Properties,Uses,Production
Uses
(2R)-N-Boc-4-oxo-proline was used as a reactant in the preparation of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides which are potent factor Xa inhibitors with increased human half life. Also used in the synthesis of azacyclic FTY720 analogues which show potential for use in strategy to kill cancer cells as they restrict access to extracellular nutrients.
Synthesis
135042-12-5
364077-84-9
Step 1: Preparation of (R)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (29a). At 0 °C, (2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (14b) (51 g, 221 mmol) was dissolved in dichloromethane (2023 mL), trichloroisocyanuric acid (51.3 g, 221 mmol) and TEMPO (1.723 g, 11.03 mmol) were added. Stirring was maintained at 0°C for 30 min, then slowly warmed to room temperature and stirred overnight. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and stirring was continued for 30 min. Subsequently, dichloromethane was removed by distillation under reduced pressure. The residue was diluted with ethyl acetate (200 mL) and filtered through a diatomaceous earth plug. The filtrate was acidified with 1 M HCl (8 mL) and the organic layer was separated. The ethyl acetate layer was washed sequentially with water (4 x 200 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the white solid product (R)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (29a) (38 g, 166 mmol, 75% yield). The product was confirmed by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry (ES-).
References
[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 6, p. 2501 - 2511
[2] Patent: WO2017/59178, 2017, A1. Location in patent: Page/Page column 105
[3] Patent: WO2004/87646, 2004, A2. Location in patent: Page/Page column 63-64
[4] Patent: WO2017/117239, 2017, A1. Location in patent: Page/Page column 53; 54
(R)-4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shandong Haihui Pharmaceutical Co., Ltd. | 18861302055 | 2634809846@qq.com | China | 13 | 58 |
| SICHUAN TONGSHENG BIOPHARMACEUTICAL CO., LTD | 0838-2809458 13350585791 | pharm@biots.cn | China | 747 | 58 |
| Shanghai Hobor Chemical Co., Ltd | 13918007836 | sales@hoborchem.com | China | 423 | 60 |
| ITIC MEDCHEM(SUZHOU) CO.,LTD. | 0512-68323967 18015559028 | sales@iticmedchem.com | China | 528 | 61 |
| Beijing Ouhe Technology Co., Ltd | 13552068683 13522913783 | 2355560935@qq.com | China | 11777 | 60 |
| Haoyuan Chemexpress Co., Ltd. | 021-58950125 | info@chemexpress.com | China | 7545 | 61 |
| SynAsst Chemical. | 021-60343070 | China | 12731 | 55 | |
| SINO High Goal Chemical Technology Co., Ltd. | 021-57646680 18306277365 | sunkai@chembiobanksh.com | China | 2039 | 55 |
| Tianjin Chempharmatech Co.,Ltd. | 022-66211079 13212288319 | sales@chempharmatech.com | China | 943 | 55 |
| Amatek Scientific Co. Ltd. | 0512-56316828 4008675858 | sales@amateksci.com | China | 9849 | 55 |
View Lastest Price from (R)-4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
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2020-01-14 | (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
364077-84-9
|
$7.00 | 1KG | 99% | 1000kg | Career Henan Chemical Co |
-
- (R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
364077-84-9
- $7.00
- 99%
- Career Henan Chemical Co
