Hydrochloric Acid → Ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate

HRID 1427102노트

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HRID 1427102 반응식
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:33])=[C:15]([CH:32]=3)[C:16]([NH:18][C:19]3[C:29]([CH3:30])=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][C:20]=3[CH3:31])=[O:17])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC(C)=O.O.[OH-].[Na+]>[CH3:31][C:20]1[CH:21]=[C:22]([CH:28]=[C:29]([CH3:30])[C:19]=1[NH:18][C:16](=[O:17])[C:15]1[CH:32]=[C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:12]=[CH:13][C:14]=1[CH3:33])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 86707334Ethyl 4-[[5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoate

생성물 1

HCID 86707335Ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate수율 61%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

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온도
60 °C

실험 절차

To a solution of ethyl 4-[[5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoate (205 mg, 452.99 μmoles) in acetone (5 ml) is added a mixture of 5M HCl (1 mL) in H2O (1 mL) and heated to 60° C. After 12 hours, the mixture is cooled to ambient temperature, diluted with 2M NaOH to pH 6 and extracted with ethyl acetate. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 0-40% ethyl acetate in hexane to afford the title compound as an off-white foam (0.11 g, 61%). Mass spectrum (m/z): 409.2 (M+1).

후처리

  1. temperaturethe mixture is cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (silica gel)

출처 및 근거

ORD 기록
ord-634ddc299a5a441d96c41f2fc4d5c7d7
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933098B2

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