Lithium Hydroxide → 3-{4-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acid

HRID 748978노트

반응식

HRID 748978 반응식
C[O:2][C:3](=[O:34])[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]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.O>[C:30]([O:29][C:27]([NH:26][CH:20]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:7][CH:8]=2)=[CH:14][CH:15]=1)=[O:28])([CH3:32])([CH3:31])[CH3:33]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 59762818HCID 59762818, 화합물

생성물 1

HCID 597628113-{4-[4-(2-Tert-butoxycarbonylamino-2-dimethylcarbamoyl-ethyl)-phenoxy]-phenyl}-propionic acid수율 103.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Amide 5 (8.4 g, 17.0 mmol) was dissolved in THF (60 mL) and diluted with water (60 mL). Lithium hydroxide (1.66 g, 69.0 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 6 (8.0 g, 97%). 1H NMR (400 MHz, DMSO-d6): 12.15 (br, 1H), 7.22 (overlapped d, J=8.4 Hz, 4H), 7.06 (d, J=8.4 Hz, 1H), 6.88 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 4.53 (m, 1H), 2.91 (s, 3H), 2.73-2.83) (m, 9H), 1.31 (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-4da061695679419fb2d8ea42faa8ea43
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399786B2

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