p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 178462319, compound

HRID 727705Notes

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]([CH3:47])[C@H:44]([C:48](=[O:69])[NH:49][CH2:50][CH2:51][N:52](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C:53]([NH2:55])=[NH:54])[CH2:43]1>>[NH:52]([CH2:51][CH2:50][NH:49][C:48]([C@@H:44]1[CH2:43][C@H:42]([S:41][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]([OH:23])=[O:22])[CH2:46][N:45]1[CH3:47])=[O:69])[C:53]([NH2:55])=[NH:54]

Participants

Reactant 2

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

HCID 88299101HCID 88299101, compound

Product 1

HCID 178462319HCID 178462319, 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-1-methyl-2-[2-(4-nitrobenzyloxycarbonylguanidino)ethylcarbamoyl]pyrrolidine (prepared as described in Preparation 103) as starting materials, in relative proportions similar to those used in that Example, to obtain the title compound.

Sources & evidence

ORD record: ord-2c9fe7d34ddc41c89e4ec2c38fd72e68
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712267

Reaction notes

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