Sodium Hydroxide → HCID 59146032, compound

HRID 1512786Notes

Reaction equation

HRID 1512786 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:10][C:11]1[CH:12]=[C:13]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:27]=[CH:28][CH:29]=[C:30]4[C:34]=3[N:33]([CH3:35])[CH:32]=[C:31]4[CH:36]=O)[N:22]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH:18]([CH3:20])[CH3:19].[OH-].[Na+]>C(O)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:27]=[CH:28][CH:29]=[C:30]4[C:34]=3[N:33]([CH3:35])[CH:32]=[C:31]4[CH2:36][NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:22]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH:18]([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 591461277-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 59146032HCID 59146032, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

ethyl β-alaninate hydrochloride (768 mg) and 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D61) (396 mg) was added to a solution of NaOH (200 mg) in ethanol (10 mL). After stirring for 0.5 hour, ethanol was evaporated off and then dichloromethane (40 mL) containing AcOH (0.5 mL) was added to the residue. NaBH(OAc)3 (1.06 g) was added to the above mixture. The reaction mixture was stirred at room temperature overnight and then terminated 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 ethyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-6-alaninate (D78) (288 mg) as a yellow solid. δH (CDCl3, 400 MHz): 1.24 (3H, t), 1.46 (6H, d), 1.74 (1H, br s), 2.78 (2H, t), 3.25 (2H, t), 3.74 (3H, s), 4.31 (2H, s), 4.69-4.76 (1H, m), 7.07 (1H, d), 7.70 (1H, t), 7.60 (1H, d), 7.80 (1H, dd), 8.02 (1H, dd), 8.22 (1H, d). MS (ES): C26H29ClN4O4 requires 496; found 380.2 (M—NHCH2CH2COOEt+).

Workup

  1. customethanol was evaporated off
  2. additiondichloromethane (40 mL) containing AcOH (0.5 mL)
  3. additionwas added to the residue
  4. additionNaBH(OAc)3 (1.06 g) was added to the above mixture
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. customterminated by saturated NaHCO3 solution
  7. customThe organic layer was separated
  8. washwashed with water and brine
  9. customAfter the solvent was evaporated off the residue
  10. customwas purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-780373206bc34e5aa11af2bb05eb5578
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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