Citric Acid → HCID 69235620, 화합물

HRID 394556노트

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HRID 394556 반응식
C[O:2][C:3](=O)[CH2:4][C@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Li+].C(O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:20][C:17]([O:16][C:14](=[O:15])[NH:13][C@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:4][CH2:3][OH:2])([CH3:18])[CH3:19]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 702EthanolHCID 4148881Lithium borohydride2회HCID 10447103Methyl (βR)-β-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoate

생성물 1

HCID 69235620HCID 69235620, 화합물수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution (R)-β-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzenebutanoic acid methyl ester (1.5 g, 5.1 mmol, J. Med. Chem. 1985, 28, 434) in THF (10 mL), was added lithium borohydride (218 mg, 10 mmol), followed by ethanol (10 mL), dropwise. After stirring at rt for 18 hours, an additional lithium borohydride (218 mg 10 mmol) was added and stirring continued for 6 hours. The reaction mixture was ice cooled and adjusted to pH 4 by the addition of a 10% citric acid solution. Organic solvents were removed and the resulting cloudy aqueous solution was extracted with dichloromethane. The extracts were combined, dried (MgSO4) and concentrated in vacuo to afford a clear colorless oil residue which was purified by flash chromatography on silica gel eluting with 30% ethyl acetate in hexanes to yield (1.2 g, 89%) of the title compound as a clear colorless oil. MS; (M+H)+=266

후처리

  1. stirringstirring
  2. waitcontinued for 6 hours
  3. temperaturecooled
  4. customOrganic solvents were removed
  5. extractionthe resulting cloudy aqueous solution was extracted with dichloromethane
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto afford a clear colorless oil residue which
  9. customwas purified by flash chromatography on silica gel eluting with 30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-8f6100843be8492c9361c8bd8ca5e12c
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602883B1

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