4-Methylmorpholine → N-Cbz-5-hydroxy-L-norvaline methyl ester

HRID 556389

反応式

HRID 556389 の反応式
[NH:1]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@H:2]([C:8]([O:10][CH3:11])=[O:9])[CH2:3][CH2:4][C:5](=O)[OH:6].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.CO>[CH3:11][O:10][C:8](=[O:9])[C@@H:2]([NH:1][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH2:3][CH2:4][CH2:5][OH:6]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2733408(4S)-4-{[(benzyloxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acidHCID 4311764Sodium borohydride

生成物 1

HCID 10588891N-Cbz-5-hydroxy-L-norvaline methyl ester収率 105%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-15 °C

実験手順

To a cold (−15° C.) solution of Cbz-Glu-OMe (1.5 g) in THF (70 mL) was added N-methylmorpholine (0.616 mL) followed by isobutyl chloroformate (0.731 mL) dropwise. After 30 min stirring at −15° C., NaBH4 (576 mg) was added, followed MeOH dropwise. The reaction mixture was stirred at −10° C. for 15 min and quenched by the addition of 1M KHSO4 solution. The mixture was extracted with EA. The org. phase was washed with water, dried (Na2SO4) and evaporated off to give the crude product as a colourless oil (1.5 g).

後処理

  1. stirringThe reaction mixture was stirred at −10° C. for 15 min
  2. customquenched by the addition of 1M KHSO4 solution
  3. extractionThe mixture was extracted with EA
  4. washphase was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated off

出典と根拠

ORDレコード
ord-4f1ce3f10b7442eba7e321d9768f01b5
出典データセット
uspto-grants-2011_11
特許番号
US08058263B2

関連ノート

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