Dichloromethane → HCID 86652152, compound

HRID 1519470Notes

Reaction equation

HRID 1519470 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].ClCCl.[CH3:11][NH:12][CH2:13][C:14]([O:16][CH:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:24](=[O:42])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[CH:27][C:26]=2[CH3:41])[C:19]2[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:18]1=2)=[O:15].CN1CCOCC1>C(OCC)(=O)C>[Cl:7][CH:5]([O:4][C:2]([CH2:11][NH:12][CH2:13][C:14]([O:16][CH:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:24](=[O:42])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])=[CH:27][C:26]=2[CH3:41])[C:19]2[CH:43]=[CH:44][C:45]([Cl:47])=[CH:46][C:18]1=2)=[O:15])=[O:3])[CH3:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 5213051-Chloroethyl chloroformateHCID 66733485HCID 66733485, compound

Product 1

HCID 86652152HCID 86652152, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Chloroethyl chloroformate (0.12 ml, 1.2 mmol) was added dropwise to a dichloromethane (10 ml) solution of 7-chloro-1-[2-methyl-4-(2-methylbenzamido)benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl methylaminoacetate (0.60 g, 1.2 mmol), and the mixture was cooled with ice. Then N-methylmorpholine (0.15 ml, 1.4 mmol) was gradually added dropwise thereto. After the resultant mixture was stirred at room temperature for 1 hour, the reaction mixture was diluted with ethyl acetate, washed with water and an aqueous saturated sodium chloride solution, dried over sodium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography (n-hexane:ethyl acetate) to obtain 0.67 g (93%) of 7-chloro-1-[2-methyl-4-(2-methylbenzamido)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl [(1-chloroethoxycarbonyl)methylamino]acetate as amorphous.

Workup

  1. temperaturethe mixture was cooled with ice
  2. washwashed with water
  3. dry with materialan aqueous saturated sodium chloride solution, dried over sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-c6b325f4e39144fdb0144cb408cdb0ef
Source dataset
uspto-grants-2015_07
Patent number
US09073868B2

Reaction notes

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