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

HRID 573008

反応式

HRID 573008 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 73012-Methyltetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f81bbe8e7a53400187c1f199d5bbf0ab
出典データセット
uspto-grants-2015_05
特許番号
US09029406B2

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