Acetic Anhydride → HCID 135798757, compound

HRID 1596360Notes

Reaction equation

HRID 1596360 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N+:18]([O-])=[C:17]([CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[NH:14][C:13]1=[O:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:30]C(=O)C)(=[O:29])[CH3:28]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:20][O:30][C:27](=[O:29])[CH3:28])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[NH:14][C:13]1=[O:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178434780HCID 178434780, compound

Product 1

HCID 135798757HCID 135798757, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (3RS)-3-benzyloxycarbonylamino-5,9-dimethyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one-4-oxide (2.83 g,) and acetic anhydride (7.6 ml, 10 eq.mol) in methylene chloride (60 ml) was stirred for 4 days. From the reaction mixture methylene chloride was removed in vacuo. To the residue was added a mixture (60 ml) of diisopropyl ether and n-hexane (1:1). The resultant crystalline powder was collected by filtration and washed with diisopropyl ether to give (3RS)-3-benzyloxycarbonylamino-5-acetoxymethyl-9-methyl-2,3-dihydro-1H-1,4-benzodiazepine-2-one (2.26 g, 71.1%) as a crystalline powder.

Workup

  1. customFrom the reaction mixture methylene chloride was removed in vacuo
  2. additionTo the residue was added a mixture (60 ml) of diisopropyl ether and n-hexane (1:1)
  3. filtrationThe resultant crystalline powder was collected by filtration
  4. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-51e6ec6aef42433386dc525c98a19483
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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