Ethyl Acetate → trans-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamic acid chloromethyl ester

HRID 16159

Reaction equation

HRID 16159 reaction equation
C(=O)(O)[O-].[Na+].[Cl:6][C:7]1[CH:26]=[CH:25][C:10]2[O:11][C:12]3[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=3[C@@H:14]3[C@H:19]([NH2:20])[CH2:18][CH2:17][CH2:16][N:15]3[C:9]=2[CH:8]=1.Cl[C:28]([O:30][CH2:31][Cl:32])=[O:29].C(OCC)(=O)C>C(Cl)Cl>[Cl:32][CH2:31][O:30][C:28](=[O:29])[NH:20][C@H:19]1[C@@H:14]2[N:15]([C:9]3[CH:8]=[C:7]([Cl:6])[CH:26]=[CH:25][C:10]=3[O:11][C:12]3[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=32)[CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 62754Chloromethyl chloroformateHCID 516892Sodium BicarbonateHCID 70883458trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

Product 1

HCID 86599867trans-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamic acid chloromethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 μL of saturated aq. sodium bicarbonate was added to trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (9.5 mg, 0.03 mmol) and chloromethyl chloroformate (64.2 μL, 0.42 mmol) in 250 μL of CH2Cl2. The resulting mixture was stirred at room temperature for 18 h. Subsequently, ethyl acetate was added and the organic layer was washed with water, dried (Na2SO4) and evaporated to give trans-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamic acid chloromethyl ester (9.9 mg, 88%). Data: (m/z)=393 (M+H)+.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-65d4b72cde144581bdaebd6c8dfe058f
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Linked notes

Loading…