Acetic Acid → HCID 86652153, compound

HRID 1519471Notes

Reaction equation

HRID 1519471 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-1b2edc8ebe004c3bbb02750d211ecad2
Source dataset
uspto-grants-2015_07
Patent number
US09073868B2

Reaction notes

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