Sodium Hydroxide → HCID 44548735, compound

HRID 1512917Notes

Reaction equation

HRID 1512917 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][NH:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>O1CCCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59146032HCID 59146032, compound

Product 1

HCID 44548735HCID 44548735, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-β-alaninate (D78) (287 mg) in tetrahydrofuran (5 mL) and ethanol (5 mL) stirred at 20° C. was added a solution of sodium hydroxide (60 mg) in water (5 mL) in one charge. The reaction mixture was stirred at 20° C. overnight. The reaction mixture was concentrated and then H2SO4 (0.1 M) solution was added dropwise until no further white precipitate was formed. The solid was filtered and recrystallized from EtOAc to afford N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-β-alanine (E58) (130 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 2.28 (2H, t), 2.91 (2H, t), 3.68 (3H, s), 4.11 (2H, s), 4.88-4.91 (1H, m), 7.23 (1H, t), 7.45-7.50 (3H, m), 7.96 (1H, dd), 8.14 (1H, dd), 8.21 (1H, d). MS (ES): C24H26ClN4O4 requires 468. found 380.1 (M—NHC2H4COOH+).

Workup

  1. additioncharge
  2. concentrationThe reaction mixture was concentrated
  3. additionH2SO4 (0.1 M) solution was added dropwise until no further white precipitate
  4. customwas formed
  5. filtrationThe solid was filtered
  6. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-7bf5451c257640b59a27741ef47641f3
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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