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

HRID 1445761Notes

Reaction equation

HRID 1445761 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

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

Conditions

Temperature
0 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-abf392cb93b945ac93ee06688db8ca0d
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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