(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidine → HCID 57290625, compound

HRID 863351Notes

Reaction equation

HRID 863351 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([C@@H:5]1[CH2:9][C@H:8]([SH:10])[CH2:7][N:6]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:12])=[O:4].[Si:25]([O:32][C@@H:33]([C@H:35]1[C:62](=[O:63])[N:37]2[C:38]([C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[CH:55][CH:54]=3)=[O:50])=[C:39](S(C3C=CC=CC=3)=O)[CH2:40][C@@H:36]12)[CH3:34])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>>[Si:25]([O:32][C@@H:33]([C@H:35]1[C:62](=[O:63])[N:37]2[C:38]([C:49]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[CH:55][CH:54]=3)=[O:50])=[C:39]([S:10][C@H:8]3[CH2:9][C@@H:5]([C:3](=[O:4])[N:2]([CH3:24])[CH3:1])[N:6]([C:11]([O:13][CH2:14][C:15]4[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=4)=[O:12])[CH2:7]3)[CH2:40][C@@H:36]12)[CH3:34])([C:28]([CH3:31])([CH3:29])[CH3:30])([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 10871907(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidineHCID 57003287HCID 57003287, compound

Product 1

HCID 57290625HCID 57290625, compoundYield 89%

Procedure

Following a procedure similar to that described in Example 18, but using (2S,4S)-2-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-mercaptopyrrolidine and the crude 4-nitrobenzyl (5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-2-phenylsulfinyl-1-carbapen-2-em-3-carboxylate (prepared as described in Preparation 47, but used before purification by column chromatography) as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained as a foam-like solid in a yield of 89%.

Sources & evidence

ORD record
ord-2557312b7e6840fe9c64ceab945a7501
Source dataset
uspto-grants-1998_02
Patent number
US05719275

Reaction notes

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