p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate → HCID 22881556, compound

HRID 727709Notes

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](=[O:82])[NH:61][CH:62]2[CH2:65][N:64]([C:66](=[NH:81])[NH:67]C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:63]2)[CH2:43]1>>[C:66]([N:64]1[CH2:63][CH:62]([NH:61][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:82])[CH2:65]1)(=[NH:67])[NH2:81]

Participants

Reactant 2

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

HCID 140386403HCID 140386403, compound

Product 1

HCID 22881556HCID 22881556, 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 32) and (2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[1-(4-nitrobenzyloxycarbonylamidino)azetidin-3-ylcarbamoyl]pyrrolidine (prepared as described in Preparation 112) as starting materials, in relative proportions similar to those used in that Example, to obtain the title compound.

Sources & evidence

ORD record: ord-e34535edc3b34b6b9fcd369b68ddbb8d
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712267

Reaction notes

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