Dichloromethane → 3-{4-[4-(2-Amino-2-dimethylcarbamoylethyl)-phenoxy]-phenyl}-propionic acid hydrochloride

HRID 748982노트

반응식

HRID 748982 반응식
C(OC([NH:8][CH:9]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1)=O)(C)(C)C.C(Cl)[Cl:35]>>[ClH:35].[NH2:8][CH:9]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1

참가 물질

3

반응물 2

HCID 6344DichloromethaneHCID 597628113-{4-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acid

생성물 1

HCID 159824543-{4-[4-(2-Amino-2-dimethylcarbamoylethyl)-phenoxy]-phenyl}-propionic acid hydrochloride수율 87%

반응 조건

온도
2.5 °C

실험 절차

The acid compound 6 (0.8 g) was dissolved in CH2Cl2 (20 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temperature for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×25 mL), decanted, and dried to yield the desired compound 10 as a white amorphous solid (0.6 g, 87%). 1H NMR (DMSO-d6): 12.20 (br, 1H), 7.24 (d, J=8.4 Hz, 2H), 7.21 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.8 Hz, 2H), 6.90 (d, J=8.0 Hz, 2H), 4.53 (m, 1H), 3.04 (dd, J=13.2 and 6.0 Hz, 1H), 2.95 (dd, J=14.0 and 8.0 Hz, 1H), 2.81 (m, 5H), 2.71 (s, 3H), 2.53 (t, J=7.6 Hz, 2H). LCMS (m/e): Obsd. 357.0, Calcd. 356.42

후처리

  1. customHydrogen chloride gas was bubbled through this solution for 20 min
  2. customThe excess HCl was degassed
  3. customthe CH2Cl2 was removed
  4. customThe residual solid was triturated with EtOAc (2×25 mL)
  5. customdecanted
  6. customdried

출처 및 근거

ORD 기록
ord-704b384940c84562afa8c148aac204b7
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399786B2

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