Ethyl chloroformate → 1-[3-[[(phenoxy)carbonyl]thio]butanoyl]-L-proline

HRID 262566Notes

Reaction equation

[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(OCC)=O.S[CH2:18][CH2:19][CH2:20][C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=[O:26])=[O:22].[SH:31]CCC(N1CCC[C@H]1C(O)=O)=O>>[O:7]([C:8]([S:31][CH:19]([CH3:18])[CH2:20][C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([OH:27])=[O:26])=[O:22])=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 4

HCID 10928Ethyl chloroformate

HCID 15891Phenyl chloroformate

HCID 999781-(3-Mercapto-1-oxopropyl)-L-proline

HCID 228203034-mercaptobutanoyl-L-proline

Product 1

HCID 543492741-[3-[[(phenoxy)carbonyl]thio]butanoyl]-L-proline

Procedure

By substituting phenylchloroformate for the ethyl chloroformate and 4-mercaptobutanoyl-L-proline for the 3-mercaptopropanoyl-L-proline in the procedure of Example 58, 1-[3-[[(phenoxy)carbonyl]thio]butanoyl]-L-proline is obtained.

Sources & evidence

ORD record: ord-326a1ee912b444d69649da56d9a19bb4
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04154840

Reaction notes

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