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| | (2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Basic information |
| Product Name: | (2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID | | Synonyms: | (2R,4S)-N-Boc-trans-4-hydroxy-D-proline;(2R,4S)-N-Boc-cis-4-hydroxy-D-proline;Boc-D-trans-Hyp-OH;N-Boc-trans-4-hydroxy-D-proline 95+%;(2R,4S)-N-Boc-4-hydroxy-D-proline;(2R,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;N-Boc-trans-D-Hyp-OH;1-tert-Butoxycarbonyl-(2R,4S)-4-hydroxypyrrolidine-2-carboxylic acid | | CAS: | 147266-92-0 | | MF: | C10H17NO5 | | MW: | 231.25 | | EINECS: | 803-000-6 | | Product Categories: | | | Mol File: | 147266-92-0.mol |  |
| | (2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Chemical Properties |
| Melting point | 123°C | | Boiling point | 390.9±42.0 °C(Predicted) | | density | 1.312±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 3.80±0.40(Predicted) | | form | solid | | color | White | | Optical Rotation | [α]/D +70°, c = 0.617 g/mL in methanol | | Major Application | peptide synthesis | | InChI | 1S/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7/m0/s1 | | InChIKey | BENKAPCDIOILGV-PKPIPKONSA-N | | SMILES | CC(C)(C)OC(=O)N1C[C@@H](O)CC1C(O)=O |
| Hazard Codes | Xi | | Risk Statements | 36 | | Safety Statements | 26 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 2933998090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2 |
| | (2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Usage And Synthesis |
| Chemical Properties | White powder | | Uses | Boc protected Proline derivative. | | reaction suitability | reaction type: Boc solid-phase peptide synthesis | | Synthesis | General procedure for the synthesis of N-BOC-trans-4-hydroxy-D-proline from di-tert-butyl dicarbonate and L-hydroxyproline:
Step A: Preparation of (4β)-1-Boc-4-hydroxy-L-proline
1. dissolve L-hydroxyproline (5.08 g, 38.77 mmol) in a solvent mixture of 1N NaOH solution (40 mL) and 1,4-dioxane (40 mL).
2. Di-tert-butyl dicarbonate (9.3 g, 42.6 mmol) was added drop-wise to the above solution at 0 °C.
3. The reaction mixture was stirred at room temperature for 8 hours. 4.
4. After completion of the reaction, the mixture was concentrated under vacuum to remove the solvent.
5. The concentrated mixture was acidified with 1N HCl and then extracted with EtOAc.
6. The organic extract was washed with brine, dried over MgSO4 and filtered.
7. Finally, the filtrate was concentrated under vacuum to give N-BOC-trans-4-hydroxy-D-proline (8.84 g, 99% yield).
MS [M + H] = 232 (M + 1). | | IC 50 | Non-cleavable Linker | | References | [1] Patent: WO2010/56022, 2010, A2. Location in patent: Page/Page column 21 |
| | (2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Preparation Products And Raw materials |
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