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

HRID 1445761ノート

反応式

HRID 1445761 の反応式
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

参加物

6

反応物 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 27340264-Bromo-2-fluorobenzoyl chlorideHCID 686989202-Amino-4-(benzyloxy)butanoic acid hydrochloride2 回

生成物 1

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

試薬・触媒・溶媒 1

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

反応条件

温度
0 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-abf392cb93b945ac93ee06688db8ca0d
出典データセット
uspto-grants-2010_02
特許番号
US07666871B2

反応ノート

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