3-{4-[4-(Tert-butoxycarbonylaminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid → 3-{4-[4-(Aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid

HRID 749008노트

반응식

HRID 749008 반응식
C(OC([NH:8][CH:9]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1)=O)(C)(C)C>C(Cl)Cl>[NH2:8][CH:9]([C:28](=[O:32])[N:29]([CH3:30])[CH3:31])[C:10]1[CH:27]=[CH:26][C:13]([O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)=[CH:12][CH:11]=1

참가 물질

3

반응물 1

HCID 597511203-{4-[4-(Tert-butoxycarbonylaminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid

생성물 1

HCID 159825823-{4-[4-(Aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid수율 64.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
2.5 °C

실험 절차

The acid compound 33 (0.3 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 temp 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 37 as a white amorphous solid (0.15 g, 59%). 1H NMR (400 MHz, DMSO-d6): 12.2 (br, 1H), 7.47 (d, J=9.2 Hz, 2H), 7.29 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 5.49 (s, 1H), 2.90 (s, 3H), 2.81-2.84 (m, 5H), 2.54 (t, J=8.0 Hz, 2H).

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-261f774d7eb04d2aae13da042cf248ec
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399786B2

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