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Lithium Hydroxide → 3-(4-{4-[2-Dimethylcarbamoyl-2-(toluene-4-sulfonylamino)-ethyl]-phenoxy}-phenyl)-propionic acid

HRID 748997
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HRID 748997 반응식
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([C:32](=[O:36])[N:33]([CH3:35])[CH3:34])[NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.O>[CH3:35][N:33]([CH3:34])[C:32]([CH:20]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:23])=[O:24])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[CH:11][CH:10]=2)=[CH:18][CH:17]=1)=[O:36]
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참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 691137573-(4-{4-[2-Dimethylcarbamoyl-2-(toluene-4-sulfonylamino)-ethyl]-phenoxy}-phenyl)-propionic acid methyl ester

생성물 1

HCID 159825783-(4-{4-[2-Dimethylcarbamoyl-2-(toluene-4-sulfonylamino)-ethyl]-phenoxy}-phenyl)-propionic acid수율 102.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028
Tetrahydrofuran
용매

실험 절차

The sulfonamide compound 24 (0.9 g, 1.72 mmol) was dissolved in THF (10 mL) and diluted with water (10 mL). Lithium hydroxide (0.16, 6.86 mmol) was added and the reaction mixture was stirred at room temperature for about 2 h. The THF was evaporated and the resulting aqueous layer was acidified with 2.0 M HCl and extracted into EtOAc (2×25 mL). The organic layer was washed with water (1×25 mL) and brine (1×25 mL), dried and concentrated to yield the desired acid compound 25 (0.9 g, quantitative). 1H NMR (400 MHz, DMSO-d6): 12.2 (br, 1H), 8.05 (d, J=9.2 Hz, 1H), 7.54 (d, J=8.4 Hz, 2H), 7.29 (d, J=7.6 Hz, 2H), 7.22 (d, J=8.8 Hz, 2H), 7.10 (d, J=8.8 Hz, 2H), 6.88 (d, J=8.4 Hz, 2H), 6.82 (d, J=8.8 Hz, 2H), 4.28 (m, 1H), 2.75-2.81 (m, 3H), 2.69 (s, 3H), 2.60 (dd, J=13.2 and 7.6 Hz, 1H), 2.52 (t, J=8.0 Hz, 2H), 2.35 (s, 3H). LCMS (m/e): Obsd. 526, Calcd. 525.62

후처리

  1. customThe THF was evaporated
  2. extractionextracted into EtOAc (2×25 mL)
  3. washThe organic layer was washed with water (1×25 mL) and brine (1×25 mL)
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-061ceede249c45fab48e3f13fa0166b5
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07399786B2

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