Triethylamine → benzyl (3R)-3-[(biphenyl-4-carbonyl)amino]-4-(3-cyanophenoxy)butyrate

HRID 747702노트

반응식

HRID 747702 반응식
Cl.[NH2:2][C@@H:3]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(N(CC)CC)C.[C:32]1([C:38]2[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O.O>[C:38]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:39]=[CH:40][C:41]([C:42]([NH:2][C@@H:3]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=2)[CH2:4][C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])=[O:43])=[CH:45][CH:46]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 86760704benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride

생성물 1

HCID 86760703benzyl (3R)-3-[(biphenyl-4-carbonyl)amino]-4-(3-cyanophenoxy)butyrate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

310 mg (1.0 mmol) of benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride was dissolved in 10 ml of dimethylformamide. 0.18 ml (1.3 mmol) of triethylamine was added to the solution. 282 mg (1.3 mmol) of 4-phenylbenzoyl chloride was added to the resultant mixture under cooling with ice, and they were stirred for 30 minutes. The temperature was elevated to room temperature, and the reaction mixture was stirred for additional 2 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

후처리

  1. temperatureunder cooling with ice, and they
  2. customwas elevated to room temperature
  3. stirringthe reaction mixture was stirred for additional 2 hours
  4. customThe reaction liquid
  5. extractionAfter the extraction with ethyl acetate
  6. washthe organic layer was successively washed with water, 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by the silica gel column chromatography

출처 및 근거

ORD 기록
ord-906c86771629420f8b5e9fcf54407058
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396844B1

반응 노트

불러오는 중…