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Acetic Acid → (2S,4R)-2-[2-(hydroxymethyl)thiazol-4-yl]-4-(methanesulfonyloxy)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37273
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인쇄 미리보기

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HRID 37273 반응식
[CH:1]([C:3]1[S:4][CH:5]=[C:6]([C@@H:8]2[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][N:9]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[N:7]=1)=[O:2].[BH4-].[Na+].C(O)(=O)C>CO.O1CCCC1>[OH:2][CH2:1][C:3]1[S:4][CH:5]=[C:6]([C@@H:8]2[CH2:12][C@@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][N:9]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[N:7]=1
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6

반응물 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 15077762(2S,4R)-2-(2-formylthiazol-4-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

생성물 1

HCID 15077763(2S,4R)-2-[2-(hydroxymethyl)thiazol-4-yl]-4-(methanesulfonyloxy)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine수율 92.1%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of (2S,4R)-2-(2-formylthiazol-4-yl)-4-methanesulfonyloxy-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (2.26 g) in a mixture of methanol (30 ml) and tetrahydrofuran (30 ml) was added sodium borohydride (94 mg) at 0° C. After stirring at 0° C. for 30 minutes, acetic acid (0.6 ml) was added to the solution. After the mixture was evaporated, the residue was dissolved in ethyl acetate, washed with water, saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated to give (2S, 4R)-2-[2-(hydroxymethyl) thiazol-4-yl]-4-(methanesulfonyloxy)-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (2.09 g)

후처리

  1. customAfter the mixture was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water, saturated sodium bicarbonate and brine successively
  4. customThe dried organic layer was evaporated

출처 및 근거

ORD 기록
ord-fa79eb52d415445fabd4caedbfaa9337
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05420122

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