(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid → (E)-(6R,7R)-7-[2-[2-(3,4-Dihydroxy-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylsulfanyl]-acetylamino]-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1597709Notes

Reaction equation

HRID 1597709 reaction equation
Br[CH2:2][C:3]([NH:5][C@@H:6]1[C:13](=[O:14])[N:12]2[C@@H:7]1[S:8][CH2:9][C:10](/[CH:18]=[C:19]1/[C:20](=[O:32])[N:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[CH2:22][CH2:23]/1)=[C:11]2[C:15]([OH:17])=[O:16])=[O:4].[Na].[SH:34][C:35]1[N:40]2[N:41]=[C:42]([C:44]3[CH:45]=[C:46]([OH:51])[C:47](=[CH:49][CH:50]=3)[OH:48])[N:43]=[C:39]2[N:38]=[C:37]([CH3:52])[CH:36]=1>CN(C)C=O>[OH:51][C:46]1[CH:45]=[C:44]([C:42]2[N:43]=[C:39]3[N:38]=[C:37]([CH3:52])[CH:36]=[C:35]([S:34][CH2:2][C:3]([NH:5][C@@H:6]4[C:13](=[O:14])[N:12]5[C@@H:7]4[S:8][CH2:9][C:10](/[CH:18]=[C:19]4/[C:20](=[O:32])[N:21]([CH2:24][C:25]6[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=6)[CH2:22][CH2:23]/4)=[C:11]5[C:15]([OH:17])=[O:16])=[O:4])[N:40]3[N:41]=2)[CH:50]=[CH:49][C:47]=1[OH:48]

Participants

4

Reactant 2

HCID 69465125(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 178429707HCID 178429707, compound

Product 1

HCID 136364242(E)-(6R,7R)-7-[2-[2-(3,4-Dihydroxy-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylsulfanyl]-acetylamino]-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-(6R,7R)-7-(2-bromo-acetylamino)-3-[1-(4-hydroxy-benzyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (see ex. C34a) (200.0 mg, 0.38 mmol) was dissolved in 4 ml N,N-dimethylformamide and 4-[7-mercapto-5-methyl-s-triazolo[1,5-a]pyrimidin-2-yl]pyrocatechol sodium salt (124.0 mg, 0.42 mmol) was added. After 5 h the reaction mixture was poured on diethyl ether and the suspension was filtered. The solid material was digerated with 10 ml ethyl acetate:water (1:1) for 1 h, filtered and dried in high vacuum.

Workup

  1. additionAfter 5 h the reaction mixture was poured on diethyl ether
  2. filtrationthe suspension was filtered
  3. filtrationfiltered
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-7cd7f00d59e745bf877cc3adb3c6c6b4
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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