Methanol → (4-Phenylamino-benzoylamino)-acetic acid

HRID 1093591ノート

反応式

HRID 1093591 の反応式
C([O:3][C:4](=[O:22])[CH2:5][NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)C.CO.O.O[Li].O>C1COCC1>[C:15]1([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][C:4]([OH:22])=[O:3])=[O:21])=[CH:9][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66591738(4-Phenylamino-benzoylamino)-acetic acid ethyl ester

生成物 1

HCID 57874498(4-Phenylamino-benzoylamino)-acetic acid収率 91.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 4-phenylamino-benzoic acid (3.0 g, 0.01401 mol) in DMF (10 mL), was added DIPEA (5.4 g, 0.04205 mol), HOBt (2.27 g, 0.01682 mol) and EDCI.HCl (6.69 g, 0.03504 mol) at ambient temperature. After 2 minutes amino-acetic acid ethyl ester hydrochloride (2.33 g, 0.01682 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the resulting precipitate was isolated by filtration, washed with water followed by hexane and dried to afford 4 g (95%) of (4-phenylamino-benzoylamino)-acetic acid ethyl ester. To a stirred solution (4-phenylamino-benzoylamino)-acetic acid ethyl ester (4 g, 0.01337 mol) in a mixture of THF (15 mL), methanol (15 mL) and H2O (8 mL) was added LiOH.H2O (2.24 g, 0.0535 mol). The resulting mixture was stirred at ambient temperature for 3 hours and then concentrated. The residue was diluted with water and acidified with 10% aqueous citric acid solution. The resulting precipitate was isolated by filtration and dried to afford 3.3 g (91%) of (4-phenylamino-benzoylamino)-acetic acid.

後処理

  1. concentrationconcentrated
  2. additionThe residue was diluted with water
  3. customThe resulting precipitate was isolated by filtration
  4. customdried

出典と根拠

ORDレコード
ord-19294c40602f475dbff835a77b97d6b4
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

読み込み中…