4-Sulfanylpyrrolidin-2-one → 4-Nitrobenzyl (1R,5S,6S)-2-[(RS)-5-oxo-3-pyrrolidinylthio]-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 863353Notes

Reaction equation

HRID 863353 reaction equation
C([N:3]([CH2:39]C)[C:4]([C:6]1C=CC=C[C:7]=1[S:12]([C:14]1[C@H:15]([CH3:38])[C@@H:16]2[C@@H:33]([C@H:34]([OH:36])[CH3:35])[C:32](=[O:37])[N:17]2[C:18]=1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])=O)=[O:5])C.SC1CNC(=O)C1>>[O:5]=[C:4]1[NH:3][CH2:39][CH:7]([S:12][C:14]2[C@H:15]([CH3:38])[C@@H:16]3[C@@H:33]([C@H:34]([OH:36])[CH3:35])[C:32](=[O:37])[N:17]3[C:18]=2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[CH2:6]1

Participants

3

Reactant 2

HCID 101299354-Sulfanylpyrrolidin-2-oneHCID 57036270HCID 57036270, compound

Product 1

HCID 572082164-Nitrobenzyl (1R,5S,6S)-2-[(RS)-5-oxo-3-pyrrolidinylthio]-6-[1(R)-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylateYield 59%

Procedure

Following a procedure similar to that described in Example 27(b), but using 4-nitrobenzyl (1R,5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-hydroxyethyl]-1-carbapen-2-em-3-carboxylate [prepared as described in Example 27(a)] and 4-mercapto-2-oxopyrrolidine as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained as a powder in a yield of 59%.

Sources & evidence

ORD record
ord-ba5a63acf9f543e2b81de40aa8147ea4
Source dataset
uspto-grants-1998_02
Patent number
US05719275

Reaction notes

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