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

HRID 24629

반응식

HRID 24629 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-bcaf08c5d8d649d39fd05e7a41426600
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855843B2

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