Benzeneacetamide → alpha-Methyl-4-methoxyphenylalanine amide

HRID 78950

反応式

HRID 78950 の反応式
C([C@H]([NH:11][C@@:12]([CH3:25])([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:13]([NH2:15])=[O:14])C1C=CC=CC=1)(=O)N.C([O-])=O.[NH4+].C1(CC(N)=O)C=CC=CC=1>CC(O)C.[Pd]>[NH2:11][C@@:12]([CH3:25])([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[C:13]([NH2:15])=[O:14]

参加物

6

反応物 3

HCID 7680BenzeneacetamideHCID 2723923Ammonium formateHCID 671670122-[(R)-(Carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide

生成物 1

HCID 67165906alpha-Methyl-4-methoxyphenylalanine amide収率 96%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 3776Isopropanol溶媒

実験手順

Method B, Transfer hydrogenolysis: Amine 3 (500 mg, 1.47 mmol, 1 eq) was dissolved in i-PrOH (5 mL) under Argon. 10% Pd/C (200 mg, 56% moisture content, 18 wt %) and ammonium formate (601 mg, 9.56 mmol, 6.5 eq.) were added. The mixture was stirred at reflux temperature for 1 h. The mixture was filtered through Celite, the filter pad was washed with EtOH (10 mL) and the filtrates were concentrated to provide 480 mg of a 1:1 mixture of desired compound (293 mg, 96%) and phenylacetamide as a white solid. 1H NMR (DMSO, 400 MHz) 1.14 (s, 3H); 2.10 (bs, 2H); 2.50 (d, J=13.1 Hz, 1H); 2.95 (d, J=13.1 Hz, 1H); 3.69 (s, 3H); 6.80 (d, J=8.5 Hz, 2H); 6.81 (bs, 1H); 6.90 (bs, 1H); 7.09 (d, J=8.5 Hz, 2H). (Phenylacetamide 3.34 (s, 2H); 7.15-7.28 (m, 6H); 7.42 (bs, 1H).). HPLC/MS 4 tR=1.96 min. MS (ESI (+)) m/z=164.2 (M-CONH2). (Phenylacetamide tR=1.76 min. MS (ESI (+)) m/z=136.2 (M+1)).

後処理

  1. temperatureat reflux temperature for 1 h
  2. filtrationThe mixture was filtered through Celite
  3. washthe filter pad was washed with EtOH (10 mL)
  4. concentrationthe filtrates were concentrated
  5. customto provide

出典と根拠

ORDレコード
ord-26340a67ae6946bfb939f57a0ef0553e
出典データセット
uspto-grants-2014_09
特許番号
US08841486B2

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