Acetic acid, 2-(2-naphthalenylthio)- → (E)-(6R,7R)-3-(1-Cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1597692Notes

Reaction equation

HRID 1597692 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23][CH2:24][C:25]([OH:27])=O.[NH2:28][C@@H:29]1[C:36](=[O:37])[N:35]2[C@@H:30]1[S:31][CH2:32][C:33](/[CH:41]=[C:42]1/[C:43](=[O:51])[N:44]([CH2:47][CH:48]3[CH2:50][CH2:49]3)[CH2:45][CH2:46]/1)=[C:34]2[C:38]([OH:40])=[O:39]>CN(C)C=O>[CH:48]1([CH2:47][N:44]2[CH2:45][CH2:46]/[C:42](=[CH:41]\[C:33]3[CH2:32][S:31][C@H:30]4[N:35]([C:36](=[O:37])[C@H:29]4[NH:28][C:25](=[O:27])[CH2:24][S:23][C:14]4[CH:15]=[CH:16][C:17]5[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=5)[CH:13]=4)[C:34]=3[C:38]([OH:40])=[O:39])/[C:43]2=[O:51])[CH2:50][CH2:49]1

Participants

5

Reactant 3

HCID 66728Acetic acid, 2-(2-naphthalenylthio)-HCID 682631,1'-CarbonyldiimidazoleHCID 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 69468177(E)-(6R,7R)-3-(1-Cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With 167.0 mg (1.03 mmol) 1,1′-carbonyldiimidazole, 225.0 mg (1.03 mmol (naphthalen-2-ylsulfanyl)-acetic acid and 300.0 mg (0.86 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 4 ml N,N-dimethylformamide.

Sources & evidence

ORD record
ord-1ca65c6d97224bed8a540b673bbe5fda
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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