Dimethylformamide diethylacetal → HCID 86742286, compound

HRID 845841Notes

Reaction equation

HRID 845841 reaction equation
C(O[CH:4](OCC)[N:5]([CH3:7])[CH3:6])C.[C:11]([O:14][CH2:15][C:16]1[CH2:23][S:22][CH:21]2[N:18]([C:19](=[O:28])[CH:20]2[NH:24][C:25]([NH2:27])=[S:26])[C:17]=1[C:29]([O:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])(=[O:13])[CH3:12]>ClCCl>[C:11]([O:14][CH2:15][C:16]1[CH2:23][S:22][C@H:21]2[N:18]([C:19](=[O:28])[C@H:20]2[NH:24][C:25]([N:27]=[CH:4][N:5]([CH3:7])[CH3:6])=[S:26])[C:17]=1[C:29]([O:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 14349716HCID 14349716, compound

Product 1

HCID 86742286HCID 86742286, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 650 mg portion of N,N-dimethylformamide diethylacetal in 10 ml of dichloromethane was added dropwise to a solution of 2 g of (6R-trans)-3-[(acetyloxy)methyl-7-[(aminothioxomethyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester in 35 ml of dichloromethane. The mixture was stirred for 20 minutes, then filtered, evaporated and the residue purified by flash chromatography using the system ethyl acetate:petroleum ether (1:1) and giving 1.08 g of the desired product.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-f8991c3e8e304291aee811d90ede7155
Source dataset
uspto-grants-1988_07
Patent number
US04760140

Reaction notes

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