1,1'-Carbonyldiimidazole → (E)-(6R,7R)-7-[2-(Benzothiazol-2-ylsulfanyl)-acetylamino]-3-(1-cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1597689Notes

Reaction equation

HRID 1597689 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[S:22][CH2:23][C:24]([OH:26])=O.[NH2:27][C@@H:28]1[C:35](=[O:36])[N:34]2[C@@H:29]1[S:30][CH2:31][C:32](/[CH:40]=[C:41]1/[C:42](=[O:50])[N:43]([CH2:46][CH:47]3[CH2:49][CH2:48]3)[CH2:44][CH2:45]/1)=[C:33]2[C:37]([OH:39])=[O:38]>CN(C)C=O>[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[S:22][CH2:23][C:24]([NH:27][C@@H:28]1[C:35](=[O:36])[N:34]2[C@@H:29]1[S:30][CH2:31][C:32](/[CH:40]=[C:41]1/[C:42](=[O:50])[N:43]([CH2:46][CH:47]3[CH2:49][CH2:48]3)[CH2:44][CH2:45]/1)=[C:33]2[C:37]([OH:39])=[O:38])=[O:26]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 805252-(2-Benzothiazolylthio)acetic acidHCID 10689147(E)-(6R,7R)-7-Amino-3-(1-cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 15405982(E)-(6R,7R)-7-[2-(Benzothiazol-2-ylsulfanyl)-acetylamino]-3-(1-cyclopropylmethyl-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

With 220.0 mg (1.35 mmol) 1,1′-carbonyldiimidazole, 304.1 mg (1.35 mmol) (benzothiazol-2-ylsulfanyl)-acetic acid and 394.8 mg (1.13 mmol) (E)-(6R,7R)-7-amino-3-(1-cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid in 7 ml N,N-dimethylformamide.

Sources & evidence

ORD record
ord-786e37033cdc423887e37cad3164ab0f
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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