Acetone → 4-Benzyloxy-2-(4-bromo-2-fluoro-benzoylamino)-butyric acid

HRID 1445761노트

반응식

HRID 1445761 반응식
Cl.[NH2:2][CH:3]([CH2:7][CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[Br:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[C:26]([F:33])[CH:25]=1.CC(C)=O>CC(C)=O.O>[CH2:10]([O:9][CH2:8][CH2:7][CH:3]([NH:2][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([Br:23])=[CH:25][C:26]=1[F:33])[C:4]([OH:6])=[O:5])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 27340264-Bromo-2-fluorobenzoyl chlorideHCID 686989202-Amino-4-(benzyloxy)butanoic acid hydrochloride2회

생성물 1

HCID 589514334-Benzyloxy-2-(4-bromo-2-fluoro-benzoylamino)-butyric acid

시약·촉매·용매 1

HCID 18366337Propan-2-one--water (1/1)용매

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온도
0 °C

실험 절차

To a stirring solution of 2-amino-4-benzyloxy-butyric acid hydrochloride salt (1.0 mmol) (See Intermediate 34) and sodium carbonate (3.0 mmol) in 1:1 acetone/water (0.5M) in a 0° C. ice bath, slowly add 4-bromo-2-fluoro-benzoyl chloride (1.2 mmol) diluted in acetone (prepared from 4-bromo-2-fluoro-benzoic acid (1.0 mmol) and oxalyl chloride (1.0 mmol) in dichloromethane using catalytic dimethylformamide). Stir for 30 minutes at 0° C. After this time, wash the reaction with 1N hydrochloric acid while extracting with ethyl acetate. Concentrate the organics in vacuo. Purify on an Isco CombiFlash® chromatography system eluting with 1% acetic acid in ethyl acetate and hexane. MS (m/e) (79Br/81Br): 410.3/412.3 (M+1)

후처리

  1. washAfter this time, wash
  2. customthe reaction with 1N hydrochloric acid
  3. extractionwhile extracting with ethyl acetate
  4. concentrationConcentrate the organics in vacuo
  5. customPurify on an Isco CombiFlash® chromatography system
  6. washeluting with 1% acetic acid in ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-abf392cb93b945ac93ee06688db8ca0d
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666871B2

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