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Lithium Hydroxide → 3-(4-{4-[3-(4-Acetyl-piperazin-1-yl)-2-tert-butoxycarbonylamino-3-oxo-propyl]-phenoxy}-phenyl)-propionic acid

HRID 748991
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HRID 748991 반응식
C[O:2][C:3](=[O:40])[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:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:21]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]3)=[O:22])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.O>[C:29]([N:26]1[CH2:27][CH2:28][N:23]([C:21](=[O:22])[CH:20]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][C:9]3[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:40])=[O:2])=[CH:7][CH:8]=3)=[CH:14][CH:15]=2)[CH2:24][CH2:25]1)(=[O:31])[CH3:30]
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참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 597628063-(4-{4-[3-(4-Acetylpiperazin-1-yl)-2-tert-butoxycarbonylamino-3-oxo-propyl]-phenoxy}-phenyl)-propionic acid methyl ester

생성물 1

HCID 597628123-(4-{4-[3-(4-Acetyl-piperazin-1-yl)-2-tert-butoxycarbonylamino-3-oxo-propyl]-phenoxy}-phenyl)-propionic acid수율 89.3%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

The amide compound 18 (2.3 g, 4.15 mmol) was dissolved in THF (20 mL) and diluted with water (20 mL). Lithium hydroxide (0.4 g, 17.0 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 (2×30 mL). The organic layer was washed with water (1×40 mL) and brine (1×40 mL), dried and concentrated to yield the desired acid compound 19 (2.0 g, 89%). 1H NMR (400 MHz, DMSO-d6): 7.16 (overlapped d, J=8.4 Hz, 2H), 7.15 (overlapped d, J=8.8 Hz, 2H), 6.91 (d, J=8.0 Hz, 2H), 6.86 (d, J=8.0 Hz, 2H), 5.47 (dd, J=12.8 and 8.4 Hz, 1H), 4.81 (m, 1H), 4.81 (m, 1H), 3.32-3.57 (m, 6H), 2.92-3.00 (m, 6H), 2.66 (t, J=6.8 Hz, 2H), 2.08 (d, J=7.6 Hz, 3H), 1.43 (s, 9H).

후처리

  1. customThe THF was evaporated
  2. extractionextracted into EtOAc (2×30 mL)
  3. washThe organic layer was washed with water (1×40 mL) and brine (1×40 mL)
  4. customdried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b35a2dce62e34910b24a2da669b04209
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07399786B2

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