(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamate → 4-Nitrobenzyl (1R, 5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-methyl-2-[2-(4-nitrobenzyloxycarbonyl)aminoethylthio]-1-carbapen-2-em-3-carboxylate

HRID 1490355Notes

Reaction equation

HRID 1490355 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.[N+:49]([C:52]1[CH:65]=[CH:64][C:55]([CH2:56][O:57][C:58]([NH:60][CH2:61][CH2:62]S)=[O:59])=[CH:54][CH:53]=1)([O-:51])=[O:50]>>[Si:38]([O:37][C@@H:35]([C@H:34]1[C:33](=[O:45])[N:18]2[C:19]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:21])=[C:15]([S:12][CH2:62][CH2:61][NH:60][C:58]([O:57][CH2:56][C:55]3[CH:64]=[CH:65][C:52]([N+:49]([O-:51])=[O:50])=[CH:53][CH:54]=3)=[O:59])[C@H:16]([CH3:46])[C@H:17]12)[CH3:36])([C:41]([CH3:43])([CH3:44])[CH3:42])([CH3:39])[CH3:40]

Participants

3

Reactant 2

HCID 3017625(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamateHCID 109745124-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfonyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate

Product 1

HCID 110070494-Nitrobenzyl (1R, 5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-methyl-2-[2-(4-nitrobenzyloxycarbonyl)aminoethylthio]-1-carbapen-2-em-3-carboxylateYield 87%

Procedure

Following a procedure similar to that described in Example 19(c), but using 4-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfonyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 42) and 2-(4-nitrobenzyloxycarbonyl)aminoethylmercaptan as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained in a yield of 87%.

Sources & evidence

ORD record
ord-a57d16ba4ced4a31a0353085922c024a
Source dataset
uspto-grants-1997_10
Patent number
US05681951

Reaction notes

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