1,1'-Carbonyldiimidazole → (E)-(6R,7R)-3-(1-Cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-7-(2-pyridin-4-ylsulfanyl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1597691Notes

Reaction equation

HRID 1597691 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[N:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:20][C:21]([OH:23])=O)=[CH:15][CH:14]=1.[NH2:24][C@@H:25]1[C:32](=[O:33])[N:31]2[C@@H:26]1[S:27][CH2:28][C:29](/[CH:37]=[C:38]1/[C:39](=[O:47])[N:40]([CH2:43][CH:44]3[CH2:46][CH2:45]3)[CH2:41][CH2:42]/1)=[C:30]2[C:34]([OH:36])=[O:35]>CN(C)C=O>[CH:44]1([CH2:43][N:40]2[CH2:41][CH2:42]/[C:38](=[CH:37]\[C:29]3[CH2:28][S:27][C@H:26]4[N:31]([C:32](=[O:33])[C@H:25]4[NH:24][C:21](=[O:23])[CH2:20][S:19][C:16]4[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=4)[C:30]=3[C:34]([OH:36])=[O:35])/[C:39]2=[O:47])[CH2:46][CH2:45]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 82574(4-Pyridylthio)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 69470055(E)-(6R,7R)-3-(1-Cyclopropylmethyl-2-oxo-pyrrolidin-3-ylidenemethyl)-8-oxo-7-(2-pyridin-4-ylsulfanyl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With 111.0 mg (0.68 mmol) 1,1′-carbonyldiimidazole, 116.0 mg (0.68 mmol) (pyridin-4-ylsulfanyl)-acetic acid and 200.0 mg (0.57 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-19b2ad734f6b4dec96b7320d899ff122
Source dataset
uspto-grants-2001_09
Patent number
US06294668B1

Reaction notes

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