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

HRID 1265223Notes

Reaction equation

HRID 1265223 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3dd022a53fb44f54a03ef1e88a8d0d63
Source dataset
uspto-grants-2003_04
Patent number
US06545029B2

Reaction notes

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