Methanol → 2-((4-Phenylphenyl)formamido)acetic acid

HRID 1093570

反応式

HRID 1093570 の反応式
C([O:3][C:4](=[O:21])[CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:8])C.CO.O.O[Li].O>C1COCC1>[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=[CH:14][C:9]([C:7]([NH:6][CH2:5][C:4]([OH:21])=[O:3])=[O:8])=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 2163299Ethyl 2-[(4-phenylphenyl)carbonylamino]acetate

生成物 1

HCID 2629432-((4-Phenylphenyl)formamido)acetic acid収率 100.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of biphenyl-4-carboxylic acid (10 g, 0.05044 mole) in DMF (50 mL), was added DIPEA (22.82 g, 0.176 mol), HOBt (7.496 g, 0.0554 mol) and EDCI.HCl (17.4 g, 0.09 mol) at ambient temperature. After 2 minutes glycine ethyl ester hydrochloride (8.45 g, 0.06 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was diluted with cold water and the resulting precipitate was isolated by filtration and dried to afford 14.26 g (99.8%) of [(biphenyl-4-carbonyl)-amino]-acetic acid ethyl ester. 1H NMR (DMSO-d6): δ9.0 (t, 1H), 8.0-7.9 (d, 2H), 7.84-7.7 (dd, 4H), 7.5 (t, 2H), 7.46-7.36 (m, 1H), 4.2-4.1 (q, 2H), 4.0 (d, 2H), 1.25 (t, 3H). To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid ethyl ester (14.26 g, 0.05 mol) in a mixture of THF (60 mL), methanol (60 mL) and H2O (30 mL) was added LiOH.H2O (12.68 g, 0.3023 mol) and the resulting mixture was stirred at ambient temperature for 1 hour. The volatiles were then evaporated and the residue was acidified with 10% aqueous HCl solution. The resulting precipitate was isolated by filtration washed with water followed by hexane and dried to afford 12.8 g (99%) of [(biphenyl-4-carbonyl)-amino]-acetic acid. 1H NMR (DMSO-d6): δ 8.0-7.85 (m, 3H), 7.8-7.7 (m, 4H), 7.55-7.45 (t, 2H), 7.45-7.35 (t, 1H), 3.5 (d, 2H).

後処理

  1. customThe volatiles were then evaporated
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. customdried

出典と根拠

ORDレコード
ord-5a6c05d1469e4604b36878f825732e38
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

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