Dichloromethane → 3-{4-[4-(2-amino-3-morpholin-4-yl-3-oxopropyl)-phenoxy]-phenyl}-N-hydroxypropionamide hydrochloride

HRID 748989노트

반응식

HRID 748989 반응식
C(OC(=O)[NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33](=[O:36])[NH:34][OH:35])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])(C)(C)C.C(Cl)[Cl:39]>>[ClH:39].[NH2:7][CH:8]([C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([NH:34][OH:35])=[O:36])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1

참가 물질

3

반응물 2

HCID 6344DichloromethaneHCID 59762804(1-{4-[4-(2-Hydroxycarbamoyl-ethyl)-phenoxy]-benzyl}-2-morpholin-4-yl-2-oxoethyl)-carbamic acid tert-butyl ester

생성물 1

HCID 159825743-{4-[4-(2-amino-3-morpholin-4-yl-3-oxopropyl)-phenoxy]-phenyl}-N-hydroxypropionamide hydrochloride수율 85%

반응 조건

온도
2.5 °C

실험 절차

The compound 16 (1.1 g) was dissolved in CH2Cl2 (30 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 17 as a white amorphous solid (0.82 g, 85%). 1H NMR (400 MHz, DMSO-d6): 10.40 (s, 1H), 7.23 (overlapped d, J=8.8 Hz, 2H), 7.20 (overlapped d, J=8.8 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 4.62 (m, 1H), 3.35-3.54 (m, 8H), 2.91-3.07 (m, 2H), 2.80 (t, J=8.0 Hz, 2H), 2.25 (t, J=8.0 Hz, 2H); LCMS: Obsd.414, Calcd. 413.47.

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-235fc3b53c5244aead12ace6ad9edc38
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399786B2

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