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Methylamine → ((1S)-1-Methylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

HRID 1872908
ノート
印刷プレビュー

反応式

HRID 1872908 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.O[N:23]1[C:27]2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:27][NH:23][C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]
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 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 7201346((1S)-1-Methylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester収率 86.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

N-t-Butoxycarbonyl-L-phenylalanine (2.65 g, 10.0 mmol) was dissolved in N,N-dimethylformamide (20 ml). To the solution were added a 40% aqueous solution (0.8 ml, 10.3 mmol) of methylamine, 1-hydroxybenzotriazole (1.48 g, 11.0 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 12.0 mmol) under cooling with ice water. The mixture was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate, washed twice with water and each once with a 10% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. After the desiccant was separated by filtration, the solvent was distilled off under reduced pressure. The resultant solids were washed with diisopropyl ether to obtain 2.41 g of the title compound.

後処理

  1. washwashed twice with water
  2. dry with materialeach once with a 10% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate
  3. customAfter the desiccant was separated by filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. washThe resultant solids were washed with diisopropyl ether

出典と根拠

ORDレコード
ord-9133a75747f24e9b847db96cd410799d
出典データセット
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06110967

反応ノート

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