Acetone → (3S)-4-Hydroxy-3-({[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

HRID 1094747

반응식

HRID 1094747 반응식
[O:1]=[C:2]1[O:6][CH2:5][C@@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.CC(C)=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>O>[OH:20][CH2:5][C@@H:4]([NH:7][C:8]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:17])[CH2:3][C:2]([OH:6])=[O:1]

참가 물질

5

반응물 3

HCID 180AcetoneHCID 10796Cesium carbonateHCID 697922Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate

생성물 1

HCID 13340757(3S)-4-Hydroxy-3-({[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In a 500 ml round-bottomed flask phenylmethyl [(3S)-5-oxotetrahydro-3-furanyl]carbamate (4.3 g, 18.28 mmol, available from Sigma-Aldrich # 419249) was dissolved in water (100 ml) and acetone (100 ml) and to this solution Cs2CO3 (10.72 g, 32.9 mmol) was added and the reaction left under stirring at room temperature for 5 hours. The solution was then transferred into a separatory funnel and washed with EtOAc (2×50 ml). The aqueous phase was then acidified to pH=2 by the addition of a 2 M HCl aqueous solution and then extracted with EtOAc (5×100 mls). The organic phase was dried (Na2SO4) and solvent removed under reduced pressure to give the title compound D1 (3.78 g) as a white solid. MS: (ES/+) m/z: 254 (M+1). C12H15NO5 requires 253. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.11 (bs, 1 H), 7.41-7.07 (m, 5 H), 5.17-4.92 (m, 2 H), 3.95-3.62 (m, 1 H), 3.42-3.22 (m, 2H), 2.55-2.40 (m, 1 H), 2.34-2.23 (m, 1 H).

후처리

  1. waitthe reaction left
  2. customThe solution was then transferred into a separatory funnel
  3. washwashed with EtOAc (2×50 ml)
  4. additionThe aqueous phase was then acidified to pH=2 by the addition of a 2 M HCl aqueous solution
  5. extractionextracted with EtOAc (5×100 mls)
  6. dry with materialThe organic phase was dried (Na2SO4) and solvent
  7. customremoved under reduced pressure

출처 및 근거

ORD 기록
ord-e541810d00e048ceb3fa3ad3bc41bdc7
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133908B2

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