p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 178485090, compound

HRID 727706Notes

Reaction equation

HRID 727706 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[CH2:67][CH2:66][N:65]([C:68](=[NH:84])[N:69](C)[C:70](OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:64][CH2:63]2)=[O:61])[CH2:43]1>>[OH:38][C@@H:36]([C@H:35]1[C:34](=[O:39])[N:19]2[C:20]([C:21]([OH:23])=[O:22])=[C:16]([S:41][C@@H:42]3[CH2:46][NH:45][C@H:44]([C:60]([N:62]4[CH2:67][CH2:66][N:65]([C:68](=[NH:84])[NH:69][CH3:70])[CH2:64][CH2:63]4)=[O:61])[CH2:43]3)[C@H:17]([CH3:40])[C@H:18]12)[CH3:37]

Participants

3

Reactant 2

HCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 88300157HCID 88300157, compound

Product 1

HCID 178485090HCID 178485090, compound

Procedure

A procedure similar to that described in Example 101 was repeated, but using 4-nitrobenzyl (1R,5R,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-2-[4-(methyl-4-nitrobenzyloxycarbonylamidino)piperazin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (prepared as described in Preparation 104 as starting materials, in relative proportions similar to those used in that Example, to obtain the title compound.

Workup

  1. customprepared
  2. customas described in Preparation 104

Sources & evidence

ORD record
ord-cfcc62542cfc42b789604d08f3c4308a
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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