Sodium Hydroxide → HCID 71239279, compound

HRID 2281168Notes

Reaction equation

HRID 2281168 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][NH:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:19][C:20]2[CH:21]=[N:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][C:24]=3C)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[OH-].[Na+].[CH2:35]1COCC1.CO>>[CH3:17][CH:16]([CH3:18])[CH2:15][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:2])=[O:32])=[O:31])=[CH:9][CH:10]=1)[NH:19][C:20]1[CH:21]=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[C:25]([CH3:35])[CH:24]=2

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 71239563HCID 71239563, compound

Product 1

HCID 71239279HCID 71239279, compoundYield 78%

Procedure

To a mixture of 3-{4-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]-benzoylamino}-propionic acid methyl ester (12) (49 mg, 0.11 mM) in 1:1 mixture of THF/MeOH (1 mL) was added 1N NaOH solution (0.283 mL, 0.283 mM). The reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated to remove organic solvent. The aqueous solution was diluted with DCM (5 mL), acidified by 1N HCl solution to pH=3-4. The organic solution was separated and the aqueous solution was extracted with 10% i-PrOH-DCM (3×5 mL). The combined organic solution were dried (Na2SO4) and concentrated to give a yellow solid product (˜78%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.93 (d, J=6.59 Hz, 3H) 0.98 (d, J=6.59 Hz, 3 H) 1.53-1.60 (m, 1 H) 1.70 (dt, J=13.72, 6.68 Hz, 1 H) 1.76-1.83 (m, 1 H) 2.43 (s, 3 H) 2.47 (t, J=7.07 Hz, 2 H) 3.35-3.46 (m, 2 H) 4.65 (t, 1 H) 7.23 (br. s., 1 H) 7.37 (d, J=8.54 Hz, 1 H) 7.41 (br. s., 1 H) 7.54 (d, J=8.29 Hz, 2 H) 7.59-7.67 (m, 2 H) 7.76 (d, J=8.29 Hz, 2 H) 8.43 (t, J=5.49 Hz, 1 H) 8.61 (d, J=2.68 Hz, 1 H), one proton was exchanged. LC-MS: m/z 420.2 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove organic solvent
  3. additionThe aqueous solution was diluted with DCM (5 mL)
  4. customThe organic solution was separated
  5. extractionthe aqueous solution was extracted with 10% i-PrOH-DCM (3×5 mL)
  6. dry with materialThe combined organic solution were dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8e4d9f057dad4683a835afc74765209b
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

Loading…