(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 1490352

Reaktionsgleichung

Reaktionsgleichung von HRID 1490352
C(N(CC)C(C1C=CC=CC=1S([C:14]1[C@H:15]([CH3:45])[C@@H:16]2[C@@H:33]([C@H:34]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH3:35])[C:32](=[O:44])[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)C.[N+:48]([C:51]1[CH:64]=[CH:63][C:54]([CH2:55][O:56][C:57]([NH:59][CH2:60][CH2:61][SH:62])=[O:58])=[CH:53][CH:52]=1)([O-:50])=[O:49]>>[Si:37]([O:36][C@@H:34]([C@H:33]1[C:32](=[O:44])[N:17]2[C:18]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)=[O:20])=[C:14]([S:62][CH2:61][CH2:60][NH:59][C:57]([O:56][CH2:55][C:54]3[CH:63]=[CH:64][C:51]([N+:48]([O-:50])=[O:49])=[CH:52][CH:53]=3)=[O:58])[C@H:15]([CH3:45])[C@H:16]12)[CH3:35])([C:40]([CH3:41])([CH3:42])[CH3:43])([CH3:39])[CH3:38]

Komponenten

3

Edukt 2

HCID 3017625(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamateHCID 110288304-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-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 92 %

Versuchsvorschrift

Following a procedure similar to that described in Example 18, but using 4-nitrobenzyl (1R, 5S,6S)-2-(2-diethylcarbamoylphenylsulfinyl)-1-methyl-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-carbapen-2-em-3-carboxylate (prepared as described in Example 39) and 2-(4-nitrobenzyloxycarbonyl)aminoethylmercaptan 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 92%.

Quellen und Nachweise

ORD-Eintrag
ord-bac07c355a0f4638a86877441422940c
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681951

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