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Methylamine → N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester

HRID 366174
ノート
印刷プレビュー

反応式

HRID 366174 の反応式
[C:1]([O:5][C:6]([N:8]([CH3:20])[C@@H:9]([C:17](O)=[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].O.O[N:23]1[C:27]2C=CC=CC=2N=N1.CN.C(Cl)Cl>CN(C)C=O.CO.O>[C:1]([O:5][C:6](=[O:7])[N:8]([CH3:20])[C@@H:9]([C:17](=[O:18])[NH:23][CH3:27])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6329MethylamineHCID 6344DichloromethaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 7015127N-Boc-N-methyl-D-phenylalanine

生成物 1

HCID 10613603N-methyl-N-((R)-1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester収率 108%

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

N-Tert-butoxycarbonyl-N-methyl-D-phenylalanine (1.22 g, 4.4 mmol), 1-hydroxybenzotriazole hydrate (0.59 g, 4.4 mmol) and 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimid hydrochloride (0.88 g, 4.6 mmol) were dissolved in N,N-dimethylformamide (25 mL) and stirred for 30 min. Methylamine (0.51 g of a 40% solution in methanol, 6.6 mmol) was added and the mixture was stirred overnight. Methylene chloride (80 mL) and water (100 mL) were added and the phases were separated. The organic phase was washed with sodium hydroxide (20 mL, 1 N), sodium hydrogensulfate (50 mL, 10%) and water (50 mL). The organic phase was dried (magnesium sulfate) and the solvent removed in vacuo to afford 1.39 g of N-methyl-N-((R)1-(methylcarbamoyl)-2-phenylethyl)carbamic acid tert-butyl ester.

後処理

  1. stirringthe mixture was stirred overnight
  2. customthe phases were separated
  3. washThe organic phase was washed with sodium hydroxide (20 mL, 1 N), sodium hydrogensulfate (50 mL, 10%) and water (50 mL)
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-52e2428165dc4c12af8fd94316e3bbce
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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