Diethyl Pyrocarbonate → HCID 70356537, compound

HRID 1110857Notes

Reaction equation

HRID 1110857 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:18][C@H:19]([C:21]([OH:23])=O)[CH3:20])[CH2:7][S:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2].[C:24]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)([CH3:27])([CH3:26])[CH3:25].CCOC(OC(OCC)=O)=O>C(N(CC)CC)C>[C:24]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:21](=[O:23])[C@H:19]([CH3:20])[NH:18][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][S:8][CH2:9][CH2:10][S:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 53807013HCID 53807013, compound

Product 1

HCID 70356537HCID 70356537, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Using 3 g of s-isomer of N-[(R)-l-ethoxycarbonyl-2-(2-phenylthioethylthio)ethyl]-alanine prepare in Reference Example 46, 1.58 of (S)-proline t-butyl ester, 1.67 g of DEPC and 1.3 ml of triethylamine and following the general procedure of Example 7, the β-isomer of the title compound was prepared as a colorless oil. Yield 3.41 g.

Sources & evidence

ORD record
ord-dc196a36ee0a41c3b93bd973d9dc648f
Source dataset
uspto-grants-1990_12
Patent number
US04977179

Reaction notes

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