(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidine → 4-Nitrobenzyl (1R, 5S,6S)-2-[(2S,4S)-2-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-pyrrolidinylthio]-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

HRID 1490350Notes

Reaction equation

HRID 1490350 reaction equation
C(N(CC)C(C1C=CC=CC=1[S:12]([C:15]1[C@H:16]([CH3:46])[C@@H:17]2[C@@H:34]([C@H:35]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH3:36])[C:33](=[O:45])[N:18]2[C:19]=1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:21])(=O)=O)=O)C.[CH3:49][N:50]([CH3:72])[C:51]([C@@H:53]1[CH2:57][C@H:56](S)[CH2:55][N:54]1[C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([N+:69]([O-:71])=[O:70])=[CH:65][CH:64]=1)=[O:60])=[O:52]>>[CH3:49][N:50]([CH3:72])[C:51]([C@@H:53]1[CH2:57][C@H:56]([S:12][C:15]2[C@H:16]([CH3:46])[C@@H:17]3[C@@H:34]([C@H:35]([O:37][Si:38]([C:41]([CH3:42])([CH3:43])[CH3:44])([CH3:39])[CH3:40])[CH3:36])[C:33](=[O:45])[N:18]3[C:19]=2[C:20]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)=[O:21])[CH2:55][N:54]1[C:59]([O:61][CH2:62][C:63]1[CH:64]=[CH:65][C:66]([N+:69]([O-:71])=[O:70])=[CH:67][CH:68]=1)=[O:60])=[O:52]

Participants

3

Reactant 2

HCID 10871907(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidineHCID 109745124-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfonyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

Product 1

HCID 104404164-Nitrobenzyl (1R, 5S,6S)-2-[(2S,4S)-2-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-pyrrolidinylthio]-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylateYield 78%

Procedure

Following a procedure similar to that described in Example 18, but using 76 mg of 4-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfonyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described it Example 42) and 46 mg of (2S,4S)-dimethylcarbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-mercaptopyrrolidine, the title compound was obtained in a yield of 78%.

Sources & evidence

ORD record
ord-d871824a856f4b48a380ff6eed37777f
Source dataset
uspto-grants-1997_10
Patent number
US05681951

Reaction notes

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