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

HRID 749008ノート

反応式

HRID 749008 の反応式
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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
2.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-261f774d7eb04d2aae13da042cf248ec
出典データセット
uspto-grants-2008_07
特許番号
US07399786B2

反応ノート

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