HCID 18657908, compound → HCID 131718807, compound

HRID 1755724Notes

Reaction equation

[CH2:1]1[C@@H:5]2[CH2:6][C:7](=[O:8])[N:4]2[C:3]([C:9]([O-:11])=[O:10])=[CH:2]1.[SH:12][C@@H:13]1[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[C@H:15]([CH:31]2[N:34]([CH3:35])[C:33](=[O:36])[CH2:32]2)[CH2:14]1>>[OH:36][C@@H:33]([C@H:6]1[C:7](=[O:8])[N:4]2[C:3]([C:9]([O:11][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:10])=[C:2]([S:12][C@@H:13]3[CH2:17][N:16]([C:18]([O:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=4)=[O:19])[C@H:15]([CH:31]4[N:34]([CH3:35])[C:33](=[O:36])[CH2:32]4)[CH2:14]3)[CH2:1][C@H:5]12)[CH3:32]

Participants

Reactant 2

HCID 18657908HCID 18657908, compound

HCID 25245027HCID 25245027, compound

Product 1

HCID 131718807HCID 131718807, compoundYield 185.8%

Procedure

The same procedure as in Example 1-1 was carried out by using p-nitrobenzyl (5R,6S)-2-diphenoxyphosphoryloxy-6-8 (R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (235 mg, 0.40 mmol) and (2S,4S)-4-mercapto-2-(N-methyl-2-azetidinon-4-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidine (149 mg, 0.41 mmol, compound of Reference Example 7) to obtain p-nitrobenzyl (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[(2S,4S)-2-(N-methyl-2-azetidinon-4-yl)-N-(p-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio]-1-carbapen-2-em-3-carboxylate (265 mg, yield: 94.5%).

Sources & evidence

ORD record: ord-3a82097e0eb54521a860b0146f1764b4
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438054

Reaction notes

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