Dicyclohexylcarbodiimide → 2-[2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

HRID 2065440

반응식

HRID 2065440 반응식
[C:1]([NH:4][CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[C:6](O)=[O:7])(=[O:3])[CH3:2].[CH3:17][O:18][C:19](=[O:30])[CH:20]([NH2:29])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:17][O:18][C:19](=[O:30])[CH:20]([NH:29][C:6](=[O:7])[CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 76957DL-Methyl tyrosinateHCID 89216N-Acetyl-DL-tyrosine

생성물 1

HCID 584275182-[2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 2-acetylamino-3-(4-hydroxy-phenyl)-propionic acid 20 (13.4 grams, 60.09 mmol) and 2-amino-3-(4-hydroxy-phenyl)-propionic acid methyl ester 1 (11.7 grams, 60.00 mmol) in anhydrous dichloro methane (100 mL) under a nitrogen atmosphere at 0° C. is added dropwise to a solution of 1,3-dicyclohexyl carbodiimide (31 grams, 150.24 mmol) in dichloro methane (75 mL). The mixture is stirred at room temperature for 6 hours. The resulting solids are filtered off. The organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL), dried over sodium sulphate, and distilled to give crude 21, which can be purified in appropriate solvent.

후처리

  1. filtrationThe resulting solids are filtered off
  2. washThe organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL)
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled
  5. customto give crude 21, which
  6. customcan be purified in appropriate solvent

출처 및 근거

ORD 기록
ord-c8cbafd3639143eba9d2458273dcd05e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288505B2

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