(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 1490354

Reaktionsgleichung

Reaktionsgleichung von HRID 1490354
[Si:1]([O:8][C@@H:9]([C@H:11]1[C:39](=[O:40])[N:13]2[C:14]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[C:15](S(C3C=CC=CC=3)=O)[C@H:16]([CH3:17])[C@H:12]12)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:41]([C:44]1[CH:57]=[CH:56][C:47]([CH2:48][O:49][C:50]([NH:52][CH2:53][CH2:54][SH:55])=[O:51])=[CH:46][CH:45]=1)([O-:43])=[O:42]>>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:39](=[O:40])[N:13]2[C:14]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])=[C:15]([S:55][CH2:54][CH2:53][NH:52][C:50]([O:49][CH2:48][C:47]3[CH:56]=[CH:57][C:44]([N+:41]([O-:43])=[O:42])=[CH:45][CH:46]=3)=[O:51])[C@H:16]([CH3:17])[C@H:12]12)[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 3017625(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamateHCID 106985434-nitrobenzyl (1R, 5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-methyl-2-phenylsulfinyl-1-carbapen-2-em-3-carboxylate

Produkt 1

HCID 110070494-Nitrobenzyl (1R, 5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-methyl-2-[2-(4-nitrobenzyloxycarbonyl)aminoethylthio]-1-carbapen-2-em-3-carboxylateAusbeute 81 %

Versuchsvorschrift

Following a procedure similar to that described in Example 21(b), but using the S-oxide isomer of lower polarity of the 4-nitrobenzyl (1R, 5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-methyl-2-phenylsulfinyl-1-carbapen-2-em-3-carboxylate (prepared as described in Preparation 2) 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 81%.

Quellen und Nachweise

ORD-Eintrag
ord-d26b7b73851b4f9c88e0cc6e06703d15
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681951

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