Tetrahydrofuran → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

HRID 573008

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HRID 573008 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17](N(OC)C)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.S([O-])(O)(=O)=O.[K+]>CC1CCCO1.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:17]=[O:18])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

시약·촉매·용매 2

HCID 962Water용매HCID 73012-Methyltetrahydrofuran용매

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온도
0 °C

실험 절차

1090 mg (3.5 mmol) Nα-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-phenylalanine-amide was dissolved in 20 mL 2-methyltetrahydrofuran and cooled to 0° C. Then 4.2 mL (4.2 mmol) of a 1M lithium aluminum hydride solution was added slowly to THF, and the reaction mixture was stirred for 30 min at 0° C. Next 5% aqueous potassium hydrogen sulfate solution was added cautiously. The batch was then diluted with water and extracted with MTBE. The organic phase was dried over magnesium sulfate and concentrated in vacuo, yielding 820 mg (94% of the theoretical) of the title compound.

후처리

  1. extractionextracted with MTBE
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f81bbe8e7a53400187c1f199d5bbf0ab
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029406B2

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