3-Pyridineacetic acid → N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester

HRID 1291765

反応式

HRID 1291765 の反応式
[C:1]([O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:11])[CH3:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21](O)=[O:22])[CH:15]=1.C(OP(C#N)(=O)OCC)C>CN(C=O)C.C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:10])[CH3:11])[NH:8][C:21](=[O:22])[CH2:20][C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 1083-Pyridineacetic acidHCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 114626tert-Butyl L-valinate

生成物 1

HCID 18659858N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

4.2 ml of triethylamine are added dropwise at 0° to a solution of 3.36 g (16 mmol) of (L)-valine-tert-butyl ester.HCl, 2 g (14.5 mmol) of 3-pyridylacetic acid and 2.17 ml (14.3 mmol) of cyanophosphonic acid diethyl ester in 20 ml of DMF. The reaction mixture is stirred for 48 h at RT, and then diluted with methylene chloride and washed with 10% citric acid as well as saturated sodium hydrogen carbonate solution. The organic phase is filtered through cotton wadding and, after removal of the solvent by evaporation, yields N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester, which is directly further used in a).

後処理

  1. washwashed with 10% citric acid as well as saturated sodium hydrogen carbonate solution
  2. filtrationThe organic phase is filtered through cotton wadding
  3. customafter removal of the solvent
  4. customby evaporation

出典と根拠

ORDレコード
ord-84fe4bba081d417da4fd906a950e4952
出典データセット
uspto-grants-1998_05
特許番号
US05753652

関連ノート

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