p-nitrobenzyl (1R,5S,6S)-2-(diphenylphosphoryloxy)-6-[(R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate → (1R,5S,6S)-2-[(2S,4S)-2-(4-Amidinohomopiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

HRID 727701Notes

Reaction equation

HRID 727701 reaction equation
C1(P(O[C:16]2[C@H:17]([CH3:40])[C@H:18]3[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]3[C:20]=2[C:21]([O:23]CC2C=CC([N+]([O-])=O)=CC=2)=[O:22])(C2C=CC=CC=2)=O)C=CC=CC=1.[SH:41][C@@H:42]1[CH2:46][N:45](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:44]([C:60]([N:62]2[CH2:68][CH2:67][CH2:66][N:65]([C:69](=[NH:84])[NH:70]C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:64][CH2:63]2)=[O:61])[CH2:43]1>>[C:69]([N:65]1[CH2:66][CH2:67][CH2:68][N:62]([C:60]([C@@H:44]2[CH2:43][C@H:42]([S:41][C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([OH:23])=[O:22])[CH2:46][NH:45]2)=[O:61])[CH2:63][CH2:64]1)(=[NH:70])[NH2:84]

Participants

3

Reactant 2

HCID 131720384p-nitrobenzyl (1R,5S,6S)-2-(diphenylphosphoryloxy)-6-[(R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylateHCID 140386396(4-nitrophenyl)methyl (2S,4S)-2-[4-[N-[(4-nitrophenyl)methoxycarbonyl]carbamimidoyl]-1,4-diazepane-1-carbonyl]-4-sulfanylpyrrolidine-1-carboxylate

Product 1

HCID 22881595(1R,5S,6S)-2-[(2S,4S)-2-(4-Amidinohomopiperazin-1-ylcarbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid

Procedure

A procedure similar to that described in Example 101 was repeated, but using 4-nitrobenzyl (1R,5S,6S)-2-(diphenylphosphoryloxy)-6-[(1R)-1-hydroxyethyl]-1-methyl -1-carbapen-2-em-3-carboxylate (prepared as described in Preparation 123) and (2S,4S)-4-mercapto-1-(4-nitrobenzyl -oxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonylamidino)homopiperazin -1-ylcarbonyl]pyrrolidine (prepared as described in Preparation 94) as starting materials, in relative proportions similar to those used in that Example, to obtain the title compound.

Sources & evidence

ORD record
ord-3e315922582042279a11197b8d695efe
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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