L-Proline 1,1-dimethylethyl ester → 1-(3-acetylthio-1-oxopropyl)-4,5-dihydro-4-hydroxy-1H-pyrrole-2-carboxylic acid

HRID 27606Notes

Reaction equation

HRID 27606 reaction equation
C([O:5][C:6](=[O:17])[C@@H:7]1[CH2:11][CH:10]([O:12]C(C)(C)C)[CH2:9][NH:8]1)(C)(C)C.C(OC(=O)[C@@H]1CCCN1)(C)(C)C.[C:30]([S:33][CH2:34][CH2:35][C:36](Cl)=[O:37])(=[O:32])[CH3:31]>>[C:30]([S:33][CH2:34][CH2:35][C:36]([N:8]1[CH2:9][CH:10]([OH:12])[CH:11]=[C:7]1[C:6]([OH:5])=[O:17])=[O:37])(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 6453108L-Proline 1,1-dimethylethyl esterHCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 545332174-tert-butoxy-L-proline tertbutyl ester

Product 1

HCID 233431911-(3-acetylthio-1-oxopropyl)-4,5-dihydro-4-hydroxy-1H-pyrrole-2-carboxylic acid

Procedure

By substituting 4-tert-butoxy-L-proline tert-butyl ester for the L-proline tert-butyl ester and 3-acetylthiopropanoyl chloride for the 3-acethylthio-2-methylpropanoyl chloride in the procedure of Example 1, 1-(3-acetylthio-1-oxopropyl)-4,5-dihydro-4-hydroxy-1H-pyrrole-2-carboxylic acid is obtained.

Sources & evidence

ORD record
ord-1a1f54ae62ec4b19a30db408707bfcf6
Source dataset
uspto-grants-1980_09
Patent number
US04221912

Reaction notes

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