Felbinac → 2-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide

HRID 1295410ノート

反応式

HRID 1295410 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH2:13][NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[CH:30][C:29]([CH2:32][C:33](O)=[O:34])=[CH:28][CH:27]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O.O>[C:26]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:14][CH2:13][CH2:12][C:11]2[CH:15]=[CH:16][C:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)=[O:34])=[CH:30][CH:31]=1

参加物

7

反応物 4

HCID 3332FelbinacHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 4238693,4-Bis(benzyloxy)phenethylamine hydrochloride

生成物 1

HCID 117858292-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The intermediate 2-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide (1) was prepared as follows: To a stirred solution of 2.85 g (7.7 mmol) of 3,4-dibenzyloxyphenethyl amine and 1.49 g (7 mmol) of 4-biphenylacetic acid in 20 ml of anhydrous dimethylformamide at 0° C., 2.5 ml (17.7 mmoles) of triethyl amine was added dropwise and then 1.4 ml (7.7 mmol) of diethyl cyanophosphonate (90% purity) was added dropwise. The reaction mixture was stirred for 22 hours and allowed to reach room temperature, and then it was poured into 300 ml of water. The precipitated solid was separated on a glass filter funnel, washed with water (3×70 ml), and air-dried overnight. This solid was recrystallized using hexanes/ethanol mixture to provide 3.1 g (84%) of grayish crystals, mp 142-144° C.

後処理

  1. customto reach room temperature
  2. customThe precipitated solid was separated on a glass
  3. filtrationfilter funnel
  4. washwashed with water (3×70 ml)
  5. customair-dried overnight
  6. customThis solid was recrystallized

出典と根拠

ORDレコード
ord-72fecbe6f4f947fca934c4a2d43b98e3
出典データセット
uspto-grants-2007_07
特許番号
US07241774B2

反応ノート

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