Sodium Hydroxide → HCID 71239510, compound

HRID 2281167Notes

Reaction equation

HRID 2281167 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]=3[CH3:30])[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:17][CH:16]([CH3:18])[CH2:15][CH:14]([C:11]1[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])=[O:31])=[CH:13][CH:12]=1)[NH:19][C:20]1[CH:21]=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71239563HCID 71239563, compound

Product 1

HCID 71239510HCID 71239510, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a mixture of 3-{4-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]-benzoylamino}-propionic acid methyl ester (44 mg, 0.1 mM) in 1:1 mixture of THF/MeOH (1 mL) was added 1N NaOH solution (0.25 mL, 0.25 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 (˜100%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.93 (d, J=6.59 Hz, 3 H) 0.98 (d, J=6.34 Hz, 3 H) 1.56 (dt, J=13.30, 6.77 Hz, 1 H) 1.71 (dt, J=13.36, 6.62 Hz, 1 H) 1.76-1.85 (m, 1 H) 2.46 (t, J=7.07 Hz, 2 H) 2.59 (s, 3 H) 3.36-3.46 (m, 2 H) 4.64 (t, J=7.07 Hz, 1 H) 7.10 (br. s., 1 H) 7.21 (br. s., 1 H) 7.26 (d, J=6.83 Hz, 1 H) 7.32 (t, J=7.56 Hz, 1 H) 7.45 (d, J=8.05 Hz, 1 H) 7.53 (d, J=8.05 Hz, 2 H) 7.76 (d, J=8.29 Hz, 2 H) 8.42 (t, J=5.49 Hz, 1 H) 8.60 (d, J=2.44 Hz, 1 H), one proton was exchanged. LC-MS: 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-fb02a9355ba34b11a84ecd7f6d4b2c31
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

Loading…