Water → Cyclopentanone

HRID 968332ノート

反応式

HRID 968332 の反応式
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

参加物

7

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11047485HCID 11047485、化合物

生成物 2

HCID 8452CyclopentanoneHCID 10970084HCID 10970084、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-add924ee654741dfab0dc22e00d4c51e
出典データセット
uspto-grants-2005_10
特許番号
US06958358B2

反応ノート

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