Sodium Hydroxide → HCID 58136460, compound

HRID 877269Notes

Reaction equation

HRID 877269 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([CH2:42][CH3:43])[CH:5]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:29]2[C:34](=[O:35])[CH2:33][O:32][C:31]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:30]2)=[CH:24][CH:23]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[CH:12]=[CH:13][CH:14]=1)=[O:7]>C1COCC1>[CH3:3][CH:4]([CH2:42][CH3:43])[CH:5]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:29]2[C:34](=[O:35])[CH2:33][O:32][C:31]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[N:30]2)=[CH:24][CH:23]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58136382HCID 58136382, compound

Product 1

HCID 58136460HCID 58136460, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.2 ml (1.20 mmol) of 1 N aqueous sodium hydroxide solution were added to a solution of 167 mg (0.30 mmol) of ethyl 3-{3-[(3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}pentanoyl)amino]phenyl}propanoate (Example 146A) in 4 ml of THF, and the mixture was stirred at room temperature overnight. After the reaction had gone to completion, the THF was removed under reduced pressure and the reaction solution was diluted with water and then adjusted to pH 2 with 1 M hydrochloric acid. The precipitated solid was filtered off, washed with water and dried under reduced pressure at 45° C. overnight. This gave 155 mg (0.29 mmol, 97% of theory) of the title compound as a mixture of isomers.

Workup

  1. customthe THF was removed under reduced pressure
  2. additionthe reaction solution was diluted with water
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customdried under reduced pressure at 45° C. overnight
  6. additionThis gave 155 mg (0.29 mmol, 97% of theory) of the title compound as a mixture of isomers

Sources & evidence

ORD record
ord-fabf3f6a710946ff94e29da5eff0026f
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

Loading…