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Lithium Hydroxide → 6-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-nicotinic acid

HRID 273439
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인쇄 미리보기

반응식

HRID 273439 반응식
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:19](=[O:23])[N:20]([CH3:22])[CH3:21])=[CH:13][CH:12]=2)=[N:6][CH:5]=1.[OH-].[Li+]>C1COCC1.O>[C:28]([O:27][C:25]([NH:24][CH:18]([C:19](=[O:23])[N:20]([CH3:21])[CH3:22])[CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][N:6]=2)=[CH:12][CH:13]=1)=[O:26])([CH3:30])([CH3:29])[CH3:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 692034916-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-nicotinic acid methyl ester

생성물 1

HCID 691138456-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-nicotinic acid수율 103.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran
용매

실험 절차

Amide 18 (1.0 g, 2.25 mmol) was dissolved in THF (10 mL) and diluted with water (10 mL). Lithium hydroxide (0.107 g, 4.5 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 (2×100 mL). The organic layer was washed with water (1×100 mL) and brine (1×100 mL), dried and concentrated to yield the desired acid compound 19 (1.0 g, 97%). 1H NMR (400 MHz, DMSO-d6): 13.1 (s, 1H), 8.64 (br, 1H), 8.27 (dd, J=8.4 and 2.0 Hz, 1H), 7.30 (d, J=8.4 Hz, 2H), 7.11 (d, J=8.8 Hz, 1H), 7.08 (m, 3H), 4.56 (m, 1H), 2.94 (s, 3H), 2.85-2.75 (m, 2H), 2.81 (s, 3H), 1.18 (s, 9H).

후처리

  1. customThe THF was evaporated
  2. extractionextracted into EtOAc (2×100 mL)
  3. washThe organic layer was washed with water (1×100 mL) and brine (1×100 mL)
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b833ddef85254a78a5c1ba847d211d93
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07456292B2

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