Sodium Hydroxide → HCID 59146180, compound

HRID 1512784Notes

Reaction equation

HRID 1512784 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].[Cl:9][C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:33]=3[NH:32][CH:31]=[C:30]4[CH:34]=O)[N:21]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH:17]([CH3:19])[CH3:18].[OH-].[Na+]>CO>[Cl:9][C:10]1[CH:11]=[C:12]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:33]=3[NH:32][CH:31]=[C:30]4[CH2:34][NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:8])[CH3:7])[N:21]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH:17]([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2733257Alanine methyl ester hydrochlorideHCID 591461517-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbaldehyde

Product 1

HCID 59146180HCID 59146180, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

L-alanine methyl ester hydrochloride (420 mg) and 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbaldehyde (D71) (382 mg) was added to a solution of NaOH (120 mg) in methanol (20 mL). After stirring for 0.5 hour, methanol was evaporated off and then after addition of AcOH (0.5 mL) in dichloromethane (40 mL), NaBH(OAc)3 (847 mg) was added. The reaction mixture was stirred at room temperature overnight and quenched by saturated NaHCO3 solution. The organic layer was separated and washed with water and brine. After the solvent was evaporated off the residue was purified by Mass Directed AutoPrep to afford methyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-D-alaninate (D76) (223 mg) as a white solid. MS (ES): C24H25ClN4O4 requires 468; found 491.1 (M+Na+).

Workup

  1. custommethanol was evaporated off
  2. additionafter addition of AcOH (0.5 mL) in dichloromethane (40 mL), NaBH(OAc)3 (847 mg)
  3. additionwas added
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. customquenched by saturated NaHCO3 solution
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. customAfter the solvent was evaporated off the residue
  9. customwas purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-c40ede8b86864c7cb27780ed02e12b7b
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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