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| | N-Boc-cis-4-Hydroxy-L-proline Basic information |
| Product Name: | N-Boc-cis-4-Hydroxy-L-proline | | Synonyms: | (2S,4S)-cis-1-N-Boc-4-hydroxy-proline, N- Boc-cis-4-hydroxypyrrolidine-2-carboxylic acid;cis-boc-Hyp-OH;cis-N-Boc-4-hydroxy-L-proline;cis-1-(tert-Butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;(2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;cis-N-Boc-4-hydroxy-L-proline, 97+%;N-Boc-cis-4-hydroxy-L-proline 95+%;CIS-BOC-L-HYP-OH | | CAS: | 87691-27-8 | | MF: | C10H17NO5 | | MW: | 231.25 | | EINECS: | 627-315-1 | | Product Categories: | Carboxylic Acids;Carboxylic Acids;Pyrrolidines | | Mol File: | 87691-27-8.mol |  |
| | N-Boc-cis-4-Hydroxy-L-proline Chemical Properties |
| Melting point | 146 °C (D) (lit.) | | alpha | -50 º (c=0.67, MeOH) | | 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 | | pka | 3.80±0.40(Predicted) | | form | Powder or Crystalline Powder | | color | White to off-white | | Optical Rotation | [α]20/D -50.0±3°, c = 0.67 in methanol | | Major Application | peptide synthesis | | InChI | 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-BQBZGAKWSA-N | | SMILES | N1(C(OC(C)(C)C)=O)C[C@@H](O)C[C@H]1C(O)=O | | CAS DataBase Reference | 87691-27-8(CAS DataBase Reference) |
| Hazard Codes | Xi,N | | Risk Statements | 36/37/38-50 | | Safety Statements | 26-36/37-60-61 | | RIDADR | UN 3077 9 / PGIII | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Acute 1
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | N-Boc-cis-4-Hydroxy-L-proline Usage And Synthesis |
| Chemical Properties | White powder | | Uses | peptide synthesis | | reaction suitability | reaction type: Boc solid-phase peptide synthesis | | Synthesis | General procedure for the synthesis of N-Boc-cis-4-hydroxy-L-proline from (S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid: An appropriate amount of solvent was added to the reaction vessel and cooled to the specified temperature. Subsequently, the reducing agent (4.0~5.0 equivalents) was added in batches, taking care to control the rate of addition to avoid violent exotherm. The progress of the reaction was monitored by HPLC during the reaction. Upon completion of the reaction, the reaction solution was slowly poured into ice water to maintain the temperature at 0~5°C. The pH was adjusted to 0~5°C with dilute hydrochloric acid. The pH was adjusted to 2~3 with dilute hydrochloric acid and then extracted with ethyl acetate (EA) (5X each time, 3 times). All organic phases were combined, washed with saturated brine and dried with anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to give the crude product. Finally, the crude product was recrystallized in a mixed solvent of ethyl acetate and alkanes to give purified N-Boc-cis-4-hydroxy-L-proline. | | References | [1] Patent: CN106543062, 2017, A. Location in patent: Paragraph 0021; 0024; 0027
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2253 - 2265
[3] Tetrahedron Letters, 1993, vol. 34, # 46, p. 7489 - 7492
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 251 - 259 |
| | N-Boc-cis-4-Hydroxy-L-proline Preparation Products And Raw materials |
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