Benzyl Bromide → N-(4-methoxybenzenesulfonyl)-D-valine benzyl ester

HRID 1006092

반응식

HRID 1006092 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@H:13]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:26]([O:15][C:14](=[O:16])[C@H:13]([NH:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH:17]([CH3:19])[CH3:18])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 1133588N-[4-methoxybenzenesulfonyl]-(D)-valine

생성물 1

HCID 15429254N-(4-methoxybenzenesulfonyl)-D-valine benzyl ester수율 83.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2(R)-(4-methoxybenzenesulfonylamino)-3-methylbutyric acid (40 g, 139.2 mmol) and cesium carbonate (85.7 g, 444 mmol) in dimethylformamide was added benzyl bromide (16.1 g, 135 mmol). The reaction mixture was stirred overnight. The dimethylformamide was removed on the rotoevaporator and the residue was dissolved in ethyl acetate (200 ml) and partitioned with an equal volume of water. The organic phase was collected and washed with an equal volume of brine. The aqueous phases were back extracted with ethyl acetate (2×150 ml), combined and dried over magnesium sulfate and condensed to provide 2(R)-(4-methoxybenzenesulfonylamino)-3-methylbutyric acid benzyl ester (42.6 g) as a white crystalline solid.

후처리

  1. customThe dimethylformamide was removed on the rotoevaporator
  2. dissolutionthe residue was dissolved in ethyl acetate (200 ml)
  3. custompartitioned with an equal volume of water
  4. customThe organic phase was collected
  5. washwashed with an equal volume of brine
  6. extractionThe aqueous phases were back extracted with ethyl acetate (2×150 ml)
  7. dry with materialdried over magnesium sulfate and condensed

출처 및 근거

ORD 기록
ord-68ce58b2be194aa8a3aee0faad7cbd96
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787559B2

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