Triethylamine → N-methoxyethoxyacetyl-(L)-valine tert-butyl ester

HRID 1291776

反応式

HRID 1291776 の反応式
C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:19])[C@H:14]([CH:16]([CH3:18])[CH3:17])[NH2:15])([CH3:11])([CH3:10])[CH3:9].[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26](O)=[O:27].C(OP(C#N)(=O)OCC)C>CN(C=O)C.C(Cl)Cl>[C:8]([O:12][C:13](=[O:19])[C@H:14]([CH:16]([CH3:17])[CH3:18])[NH:15][C:26](=[O:27])[CH2:25][O:24][CH2:23][CH2:22][O:21][CH3:20])([CH3:11])([CH3:10])[CH3:9]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 27642(2-Methoxyethoxy)acetic acidHCID 76257Diethyl cyanophosphonateHCID 114626tert-Butyl L-valinate

生成物 1

HCID 80707032N-methoxyethoxyacetyl-(L)-valine tert-butyl ester収率 81.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

At 0°, 6.4 ml (45.7 mmol) of triethylamine are added to a solution of 5 g (23.9 mmol) of (L)-valine tert-butyl ester, 2.91 g (21.7 mmol) of 2-(methoxyethoxy)-acetic acid and 3.55 g (21.7 mmol) of cyanophosphonic acid diethyl ester in 30 ml of DMF and the mixture is then stirred overnight at RT. The reaction mixture is diluted with methylene chloride, washed in succession with 10% citric acid, saturated sodium hydrogen carbonate solution and saturated sodium chloride solution and, after concentration by evaporation of the organic phase, yields 5.1 g of N-methoxyethoxyacetyl-(L)-valine tert-butyl ester, which is stirred for 1 h at RT in 22 ml of a (1:1) mixture of methylene chloride and TFA. Concentration by evaporation of the reaction solution yields the title compound in the form of a colourless oil. 1H-NMR (200 MHz, CDCl3): 10.0 (s, broad, 1H), 7.62 d, broad, 1H), 4.55 (m, 1H), 4.10 (s, 2H), 3.70 (m, 2H), 3.58 (m, 2H), 3.40 (s, 3H), 2.28 (m, 1H), 0.98 (d, J=7 Hz, 3H), 0.95 (d, J=7 Hz, 3H).

後処理

  1. washwashed in succession with 10% citric acid, saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  2. concentrationafter concentration
  3. customby evaporation of the organic phase

出典と根拠

ORDレコード
ord-6319baa8aaeb4eb9aab4cda2aff0c823
出典データセット
uspto-grants-1998_05
特許番号
US05753652

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