Water → Cyclopentanone

HRID 968332노트

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HRID 968332 반응식
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O:14][C:15]1(OC)[CH2:19][CH2:18][CH2:17][CH:16]1[O:20][C:21](=[O:38])[C@@H:22]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.C(=O)([O-])O.[Na+]>CC(C)=O>[O:14]=[C:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[O:20][C:21](=[O:38])[C@@H:22]([NH:30][C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1.[C:15]1(=[O:14])[CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11047485HCID 11047485, 화합물

생성물 2

HCID 8452CyclopentanoneHCID 10970084HCID 10970084, 화합물

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

4-Toluenesulphonic acid monohydrate (1.7 g, 9.2 mmol) was added to a stirred solution of (2S)-2-tert-butoxycarbonylamino-3-phenylpropionic acid 2,2-dimethoxycyclopentyl ester (36 g, 91.6 mmol) in acetone (450 ml) at ambient temperature. The solution was stirred for 3 days then water (600 ml) and saturated aqueous sodium hydrogen carbonate solution (200 ml) were added, then the product was extracted into ethyl acetate (600 ml). The aqueous phase was extracted with ethyl acetate (2×400 ml), then the combined ethyl acetate solutions were washed with saturated aqueous sodium chloride solution (2×150 ml), dried (Na2SO4) and the solvent removed in vacua. The residue (18.05 g) was purified by flash chromatography over silica gel eluting with a gradient of heptane:ethyl acetate 3:1→2:1. Appropriate fractions were combined and the solvents removed in vacuo to leave (2S)-2-tert-butoxycarbonylamino-3-phenylpropionic acid 2-oxocyclopentyl ester as a colourless oil (18.05 g, 40% from cyclopentanone). TLC (single UV spot, Rf=0.25, heptane:ethyl acetate 7:3), analytical HPLC with main broad peak Rt=17.9-19.2 mins, HPLC-MS (main broad UV peak with Rt=9.04-9.24 mins, 248.1 [M−Boc+2H]+, 370.2 [M+Na]+, 717.3 [2M+Na]+).

후처리

  1. extractionthe product was extracted into ethyl acetate (600 ml)
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×400 ml)
  3. washthe combined ethyl acetate solutions were washed with saturated aqueous sodium chloride solution (2×150 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed in vacua
  6. customThe residue (18.05 g) was purified by flash chromatography over silica gel eluting with a gradient of heptane:ethyl acetate 3:1→2:1
  7. customthe solvents removed in vacuo

출처 및 근거

ORD 기록
ord-add924ee654741dfab0dc22e00d4c51e
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958358B2

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