2,6-Dichlorobenzoyl chloride → n-(2,6-Dichlorobenzoyl)-d-tyrosine methyl ester

HRID 24629

反応式

HRID 24629 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].Cl.[CH3:13][O:14][C:15](=[O:26])[C@@H:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[NH2:17].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:26])[C@@H:16]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[NH:17][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:11]

参加物

5

反応物 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 134565methyl D-tyrosinate hydrochloride

生成物 1

HCID 54468447n-(2,6-Dichlorobenzoyl)-d-tyrosine methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of 2,6-dichlorobenzoylchloride (0.68 mL) in CH2Cl2 (5 mL) was added to a solution of an ice-cold solution of D-tyrosine methyl ester HCl salt (1.0 g) and DIEA (2.26 mL) in CH2Cl2 (15 mL). The mixture was stirred at room temperature for 24 h. The mixture was diluted with CH2Cl2 (50 mL) and washed successively with H2O, 1 N HCl and brine. The organic layer was dried (MgSO4) and evaporated, and the residue was recrystallized from EtOAc and hexanes to yield 1.46 g of N-(2,6-dichlorobenzoyl)-D-tyrosine methyl ester. ESMS: m/z 369 (MH+).

後処理

  1. washwashed successively with H2O, 1 N HCl and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customthe residue was recrystallized from EtOAc and hexanes

出典と根拠

ORDレコード
ord-bcaf08c5d8d649d39fd05e7a41426600
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

関連ノート

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