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

HRID 1180805노트

반응식

HRID 1180805 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-a3ba98c0cf2f4ace8495a0b33bf6580f
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282608B2

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