Hydrogen chloride-ethyl acetate → hexahydro-1,1-diphenyl-1H-oxazolo[3,4-a][1,4]diazepin-3-one

HRID 1713509Notes

Reaction equation

HRID 1713509 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][CH:5]2[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:3]1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[C:25]1([C:4]2([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:5]3[CH2:11][NH:10][CH2:9][CH2:8][CH2:7][N:6]3[C:2](=[O:1])[O:3]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 231218741,1-Dimethylethyl tetrahydro-3-oxo-1,1-diphenyl-1H-[1,3]oxazolo[3,4-a][1,4]diazepine-8(5H)-carboxylate

Product 1

HCID 23122043hexahydro-1,1-diphenyl-1H-oxazolo[3,4-a][1,4]diazepin-3-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,1-Dimethylethyl tetrahydro-3-oxo-1,1-diphenyl-1H-[1,3]oxazolo[3,4-a][1,4]diazepine-8(5H)-carboxylate (0.30 g, 0.73 mmol) was dissolved in ethyl acetate (5 mL). A 4 M hydrogen chloride/ethyl acetate solution (4 mL) was added thereto, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated, and then ethyl acetate was added to the residue. The resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound (0.16 g, yield 70%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionethyl acetate was added to the residue
  3. washThe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e504ad419b342ee845279880f7d8961
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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