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3-Amino-1-propanol → N-((1R)-1-(3-hydroxypropylcarbamoyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester

HRID 366224
ノート
印刷プレビュー

反応式

HRID 366224 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]([O:10][C:11]([N:13]([CH3:25])[C@@H:14]([C:22](O)=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.S([O-])(O)(=O)=O.[Na+]>[C:6]([O:10][C:11](=[O:12])[N:13]([C@@H:14]([C:22](=[O:23])[NH:1][CH2:2][CH2:3][CH2:4][OH:5])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:25])([CH3:7])([CH3:9])[CH3:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 90863-Amino-1-propanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7015127N-Boc-N-methyl-D-phenylalanine

生成物 1

HCID 54054214N-((1R)-1-(3-hydroxypropylcarbamoyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester収率 64.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516919Sodium Bisulfate溶媒

実験手順

3-Aminopropan-1-ol (0.39 mL, 5.12 mmol) was added at room temperature to a solution of N-tert-butoxycarbonyl-N-methyl-D-phenylalanine (1.30 g, 4.65 mmol) in N,N-dimethylformamide (40 mL). 1-Hydroxybenzotriazole monohydrate (0.63 g, 4.65 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.89 g, 4.65 mmol) were added successively. The reaction mixture was stirred for 22 h at room temperature. It was diluted with 10% sodium hydrogensulfate solution (300 mL) and extracted with ethyl acetate (4×100 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo and the crude product was purified by flash chromatography on silica (45 g) with dichloromethane/methanol (10:1) to give 1.01 g of N-((1R)-1-(3-hydroxypropylcarbamoyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester.

後処理

  1. extractionextracted with ethyl acetate (4×100 mL)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe crude product was purified by flash chromatography on silica (45 g) with dichloromethane/methanol (10:1)

出典と根拠

ORDレコード
ord-ca29408981794951a12748b33cccb0e9
出典データセット
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06127391

反応ノート

読み込み中…

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