Acetic Acid → HCID 86652153, compound

HRID 1184649Notes

Reaction equation

HRID 1184649 reaction equation
CN1CCOCC1.[C:8]([OH:11])(=[O:10])[CH3:9].Cl[CH:13]([O:15][C:16]([CH2:18][NH:19][CH2:20][C:21]([O:23][CH:24]1[CH2:30][CH2:29][CH2:28][N:27]([C:31](=[O:49])[C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:47])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[CH3:46])=[CH:34][C:33]=2[CH3:48])[C:26]2[CH:50]=[CH:51][C:52]([Cl:54])=[CH:53][C:25]1=2)=[O:22])=[O:17])[CH3:14]>O>[C:8]([O:11][CH:13]([O:15][C:16]([CH2:18][NH:19][CH2:20][C:21]([O:23][CH:24]1[CH2:30][CH2:29][CH2:28][N:27]([C:31](=[O:49])[C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:47])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[CH3:46])=[CH:34][C:33]=2[CH3:48])[C:26]2[CH:50]=[CH:51][C:52]([Cl:54])=[CH:53][C:25]1=2)=[O:22])=[O:17])[CH3:14])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 79724-MethylmorpholineHCID 86652152HCID 86652152, compound

Product 1

HCID 86652153HCID 86652153, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-methylmorpholine (0.31 ml, 2.8 mmol) was added dropwise to an acetic acid (0.32 ml, 5.6 mmol) solution 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 (0.35 g, 0.56 mmol) under cooling with ice, and the mixture was stirred at room temperature for two days. Water was added to the reaction mixture, and then the resulted precipitates were collected by filtration and air-dried. The dried product was purified by silica gel chromatography (n-hexane:ethyl acetate) to obtain 0.26 g (72%) of 7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl [(1-acetoxy-ethoxycarbonyl)methylamino]acetate as amorphous.

Workup

  1. temperatureunder cooling with ice
  2. customthe resulted precipitates
  3. filtrationwere collected by filtration
  4. customair-dried
  5. customThe dried product was purified by silica gel chromatography (n-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-bcf477a953364dd1adc6d9c0bc8be8f6
Source dataset
uspto-grants-2014_03
Patent number
US08669229B2

Reaction notes

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