Lithium hydroxide, monohydrate → 3-[4-(2-t-Butoxycarbonylamino-phenylcarbamoyl)-phenyl]-acrylic acid

HRID 1180805ノート

反応式

HRID 1180805 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([O:28]C)=[O:27])=[CH:20][CH:19]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=1)=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 72479809Methyl 3-[4-(2-t-butoxycarbonylamino-phenylcarbamoyl)-phenyl]-acrylate

生成物 1

HCID 724798123-[4-(2-t-Butoxycarbonylamino-phenylcarbamoyl)-phenyl]-acrylic acid収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution at room temperature of compound XII (560 mg, 1.41 mmol) in THF (20 ml) was added a solution of LiOH.H2O (148 mg, 3.53 mmol) in water (20 ml). After 23 h, the reaction mixture was concentrated, diluted with water and acidified with 1N HCl until pH 4–5 in order to get a white precipitate. After stirring for 15 min, the suspension was filtered off, rinsed with water, and dried to afford the title compound XIII (495 mg, 1.29 mmol, 92% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ(ppm): 9.92 (s, 1H), 8.72 (bs, 1H), AB system (δA=8.02, δB=7.90, J=7.9 Hz, 4H), 7.69 (d, J=16.3 Hz, 1H), 7.62–7.53 (m, 2H), 7.30–7.13 (m, 2H), 6.72 (d, J=16.3 Hz, 1H), 1.48 (s, 9H)

後処理

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water
  3. customto get a white precipitate
  4. filtrationthe suspension was filtered off
  5. washrinsed with water
  6. customdried

出典と根拠

ORDレコード
ord-a3ba98c0cf2f4ace8495a0b33bf6580f
出典データセット
uspto-grants-2007_10
特許番号
US07282608B2

反応ノート

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