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Beta-Alanine → 3-{4-[1-(2-Trifluoromethyl-biphenyl-4-ylmethoxyimino)-ethyl]-benzylamino}-propionic acid

HRID 547270
ノート
印刷プレビュー

反応式

HRID 547270 の反応式
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[C:7]([CH2:9][O:10][N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=2)[CH3:13])[CH:6]=[CH:5][C:4]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34].CCN(CC)CC.[BH4-].[Na+]>O1CCOCC1.O=[Mn]=O>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:8]=[C:7]([CH2:9][O:10][N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:16][CH:15]=2)[CH3:13])[CH:6]=[CH:5][C:4]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 865959961-(4-hydroxymethyl-phenyl)-ethanone O-(2-trifluoromethyl-biphenyl-4-ylmethyl)-oxime

生成物 1

HCID 729544163-{4-[1-(2-Trifluoromethyl-biphenyl-4-ylmethoxyimino)-ethyl]-benzylamino}-propionic acid

試薬・触媒・溶媒 2

HCID 14801
Manganese dioxide
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

To a suspension of MnO2 (10 eq) in dioxane is added 1-(4-hydroxymethyl-phenyl)-ethanone O-(2-trifluoromethyl-biphenyl-4-ylmethyl)-oxime (1 eq). The resulting mixture is refluxed for 10 minutes. After filtration and concentration, the residue is dissolved in MeOH and treated with β-alanine (2 eq) and Et3N (1.5 eq). The resulting mixture is heated at 50° C. for 30 minutes. After cooling to room temperature, NaBH4 (3 eq) is added in portions. Purification by preparative LCMS results in 3-{4-[1-(2-trifluoromethyl-biphenyl-4-ylmethoxyimino)-ethyl]-benzylamino}-propionic acid; 1H NMR (400 MHz, CD3OD) δ 2.28 (s, 3H), 2.75 (t, J=6.8 Hz, 2H), 3.26 (t, J=6.8 Hz, 2H), 4.22 (s, 2H), 5.30 (s, 2H), 7.26-7.77 (m, 12H). MS: (ES+): 471.1 (M+1)+.

後処理

  1. temperatureThe resulting mixture is refluxed for 10 minutes
  2. filtrationAfter filtration and concentration
  3. dissolutionthe residue is dissolved in MeOH
  4. temperatureAfter cooling to room temperature
  5. customPurification by preparative LCMS
  6. customresults in 3-{4-[1-(2-trifluoromethyl-biphenyl-4-ylmethoxyimino)-ethyl]-benzylamino}-propionic acid

出典と根拠

ORDレコード
ord-30d51bc7ec8f4b26a81dc0207b82733e
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07939519B2

反応ノート

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