Hydrochloric Acid → 9-Acetyl-4-(1-acetylazetidin-3-yl)-7-chloro-6-fluoro-2-methyl-4,5-dihydro-1,4-benzoxazepin-3(2H)-one

HRID 626862Notes

Reaction equation

HRID 626862 reaction equation
[C:1]([N:4]1[CH2:7][CH:6]([N:8]2[CH2:14][C:13]3[C:15]([F:26])=[C:16]([Cl:25])[CH:17]=[C:18]([C:19]4([CH3:24])OCC[O:20]4)[C:12]=3[O:11][CH:10]([CH3:27])[C:9]2=[O:28])[CH2:5]1)(=[O:3])[CH3:2].Cl>CO.C(OCC)(=O)C.O>[C:19]([C:18]1[C:12]2[O:11][CH:10]([CH3:27])[C:9](=[O:28])[N:8]([CH:6]3[CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:7]3)[CH2:14][C:13]=2[C:15]([F:26])=[C:16]([Cl:25])[CH:17]=1)(=[O:20])[CH3:24]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 866975524-(1-Acetylazetidin-3-yl)-7-chloro-6-fluoro-2-methyl-9-(2-methyl-1,3-dioxolan-2-yl)-4,5-dihydro-1,4-benzoxazepin-3(2H)-one

Product 1

HCID 866975539-Acetyl-4-(1-acetylazetidin-3-yl)-7-chloro-6-fluoro-2-methyl-4,5-dihydro-1,4-benzoxazepin-3(2H)-oneYield 78%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(1-acetylazetidin-3-yl)-7-chloro-6-fluoro-2-methyl-9-(2-methyl-1,3-dioxolan-2-yl)-4,5-dihydro-1,4-benzoxazepin-3(2H)-one (190 mg, 0.460 mmol) in methanol (20 mL) and was treated with 6.0 M hydrogen chloride in water (1.15 mL, 6.90 mmol) and stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated to give the desired product (132 mg, 78%) as a mixture of enantiomers that was used without further purification. LCMS calculated for C17H19ClFN2O4(M+H)+: m/z=369.1; found: 369.1.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e87b3c1ac3f54a89ab32f93d8d204ee8
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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