Sodium Hydroxide → HCID 67433611, compound

HRID 1946539Notes

Reaction equation

HRID 1946539 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][CH2:19][C:20]([O:22]CC4C=CC=CC=4)=[O:21])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:30]([CH3:32])[CH3:31])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH3:9].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:30]([CH3:32])[CH3:31])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58460148HCID 58460148, compound

Product 1

HCID 67433611HCID 67433611, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenylmethyl 3-[1-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-yl]propanoate (second isomer from chiral HPLC, 18 mg) was dissolved in Methanol (1.5 mL). 3.3 M aqueous sodium hydroxide solution (0.5 mL) was added and the reaction mixture was left to stir at RT. After stirring for 18 h, LCMS of the reaction mixture demonstrated full consumption of the starting material and the formation of the desired acid product. The reaction mixture was concentrated in vacuo and taken up in acetonitrile/water. The resulting solution was acidified to pH 5-6 and loaded onto a 20 g SCX column. The column was washed with two column volumes of acetonitrile/water and then eluted with 10% ammonia in ethanol. The basic washings were concentrated in vacuo to afford the desired product as the ammonium salt (10.1 mg). LC/MS MH+ 361/363, Rt 1.87 mins (5 min system, TFA modifier).

Workup

  1. waitthe reaction mixture was left
  2. stirringAfter stirring for 18 h
  3. customconsumption of the starting material
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. washThe column was washed with two column volumes of acetonitrile/water
  6. washeluted with 10% ammonia in ethanol
  7. concentrationThe basic washings were concentrated in vacuo

Sources & evidence

ORD record
ord-b6928cc6642c442d8d16718ec390f17c
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

Loading…