rac-(2R,4S)-4-phenylpyrrolidine-2-carboxylic acid hydrochloride → 4-Phenyl-L-proline

Reaction equation

COC1C=CC(CSCC(C)C(Cl)=S)=CC=1.Cl.[C:18]1([C@@H:24]2[CH2:28][NH:27][C@H:26]([C:29]([OH:31])=[O:30])[CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1([CH:24]2[CH2:28][NH:27][C@H:26]([C:29]([OH:31])=[O:30])[CH2:25]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 51064133rac-(2R,4S)-4-phenylpyrrolidine-2-carboxylic acid hydrochloride

HCID 542258353-[[(4-Methoxy)phenylmethyl]thio]-2-methylthiopropionyl chloride2×

Product 1

HCID 103134714-Phenyl-L-proline

Procedure

The 3-[[(4-methoxy)phenylmethyl]thio]-2-methylthiopropionyl chloride from part (a) is reacted with cis-4-phenyl-L-proline, hydrochloride to yield [1(S),4R]-1-[[(4-methoxy)phenylmethyl]thio]-2-methylthio-1-oxopropyl]-4-phenyl-L-proline.

Sources & evidence

ORD record: ord-35f63ce70f5d4f52a185dac1316501d1
Source dataset: uspto-grants-1982_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04316905

Reaction notes

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