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Phthalimide potassium salt → (2s,4r)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine

HRID 1034486
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HRID 1034486 반응식
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[CH2:16][C@@H:15]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][N:13]2[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:23])(=O)=O)=CC=1.[C:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.[K]>CN(C)C=O>[N+:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:22]([N:13]2[CH2:14][C@H:15]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:16][C@H:12]2[CH2:11][N:40]2[C:36](=[O:46])[C:37]3=[CH:45][CH:44]=[CH:43][CH:42]=[C:38]3[C:39]2=[O:41])=[O:23])=[CH:31][CH:30]=1)([O-:34])=[O:33]
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참가 물질

4

반응물 2

HCID 24194345Phthalimide potassium saltHCID 131718416(2S,4R)-1-p-nitrobenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol p-toluenesulfonate

생성물 1

HCID 57079827(2s,4r)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of (2S,4R)-1-p-nitrobenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol p-toluenesulfonate (25 g: 47.3 mmole) and potassium phthalimide (17.52 g: 2 eq.) in dimethylformamide (250 ml) is stirred at 60° C. for 7 hours. The reaction mixture is poured into ice water and filtrated. The resulting precipitate is dissolved in ethyl acetate, washed with saturated brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is recrystallized from methanol to give (2S,4R)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine (18.76 g). Yield: 79%. mp. 121° to 123° C. NMR δ(CDCl3) ppm: 2.03 to 2.60(m, 2H), 3.02(s, 3H), 3.50 to 4.15(m, 4H), 4.40 to 4.63(m, 1H), 5.10, 5.29(ABq, J=15 Hz, 2H), 5.10 to 5.30(m, 1H), 7.46 (d, J=9 Hz, 1H), 7.57(d, J=9 Hz, 1H), 7.63 to 7.88(m, 4H), 8.20(d, J=9 Hz, 2H) IR ν (CHCl3) cm-1 : 1773, 1715, 1605.

후처리

  1. filtrationfiltrated
  2. dissolutionThe resulting precipitate is dissolved in ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallized from methanol

출처 및 근거

ORD 기록
ord-226d619ced0a4dcea28656812052a0a5
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05317016

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