Bromoacetone → HCID 178468216, compound

HRID 1088639Notes

Reaction equation

HRID 1088639 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:50])[C:7]([S:25][C@@H:26]1[CH2:30][N:29]([C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=3)=[O:32])[C@H:28]([CH2:44][N:45]3[CH:49]=[CH:48][N:47]=[CH:46]3)[CH2:27]1)=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:13])[CH3:3].[Br:51][CH2:52][C:53](=[O:55])[CH3:54]>O1CCCC1>[Br-:51].[CH2:52]([N:47]1[CH:48]=[CH:49][N+:45]([CH2:44][C@@H:28]2[CH2:27][C@H:26]([S:25][C:7]3[C@H:6]([CH3:50])[C@H:5]4[N:9]([C:10](=[O:11])[C@@H:4]4[C@H:2]([OH:1])[CH3:3])[C:8]=3[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])[CH2:30][N:29]2[C:31]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=2)=[O:32])=[CH:46]1)[C:53]([CH3:54])=[O:55]

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 15086182HCID 15086182, compound

Product 1

HCID 178468216HCID 178468216, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(2S,4S)-2-(imidazol-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-4-methyl-7-oxo-1- azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.80 g) and bromoacetone (0.3 ml) in tetrahydrofuran (8 ml) was stirred at ambient temperature for 18 hours. The mixture was concentrated under reduced pressure to give crude 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(3-acetonyl-1-imidazolio)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate bromide (1.20 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4739bcff507e4745a981602b6616d8bd
Source dataset
uspto-grants-1990_10
Patent number
US04963544

Reaction notes

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