Hydrochloric Acid → N-(Ethoxycarbonyl)-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serine

HRID 1265223노트

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HRID 1265223 반응식
[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:29]([O:31]C)=[O:30])[CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1)=[O:5])[CH3:2].[OH-].[Li+].Cl>C1COCC1.CO.O>[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:29]([OH:31])=[O:30])[CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH:25][CH2:26][CH2:27][CH3:28])=[O:24])[CH:17]=2)[CH:13]=[CH:14][CH:15]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59050114Methyl N-(ethoxycarbonyl)-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serinate

생성물 1

HCID 59050116N-(Ethoxycarbonyl)-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serine

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

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온도
0 °C

실험 절차

The compound of Example 7 (100.0 mg, 0.23 mmol, 1 equiv) was dissolved in THF/MeOH/H2O (3:1:1 2.3 mL) and the solution was cooled to 0° C. followed by addition of solid lithium hydroxide (5.4 mg, 0.23 mmol, 1 equiv). The reaction mixture was allowed to reach rt and stirred for 1 hour. It was acidified with 0.1 M aqueous HCl solution to pH 3 and extracted three times with ethyl acetate. The combined organic extracts were dried over Na2SO4 and the solvents were removed under reduced pressure and the remaining crude product was purified by chromatography (SiO2; toluene/EtOH/AcOH 95:4:1). Yield 23.7 mg, 24.5%. 1H NMR (DMSO; 200 MHz) δ 13.05 (brs, 1H); 8.59 (s, 1H); 7.72 (s, 1H); 7.05 (d, 1H); 7.41-7.22 (m, 3H); 7.17-7.03 (m, 3H); 6.91 (d, 1H); 6.22 (dd, 1H); 4.49-4.81 (m, 1H); 4.30-4.19 (m, 2H); 4.0 (q, 2H); 3.04 (q, 2H); 1.49 (sextett, 2H); 1.19 (t, 3H); 0.94 (t, 3H). MS (EI) 430 (M+H), 345, 210.

후처리

  1. customto reach rt
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. customthe solvents were removed under reduced pressure
  5. customthe remaining crude product was purified by chromatography (SiO2; toluene/EtOH/AcOH 95:4:1)

출처 및 근거

ORD 기록
ord-3dd022a53fb44f54a03ef1e88a8d0d63
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545029B2

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