Hydrochloric Acid → HCID 71240119, compound

HRID 705438Notes

Reaction equation

HRID 705438 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH:5]([NH:13][C:14]([C:16]1[N:17]=[C:18]([Br:21])[S:19][CH:20]=1)=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].[OH-].[Na+].O.Cl>CO>[Br:21][C:18]1[S:19][CH:20]=[C:16]([C:14]([NH:13][CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:12])[CH2:4][C:3]([OH:22])=[O:2])=[O:15])[N:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 71239908HCID 71239908, compound

Product 1

HCID 71240119HCID 71240119, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.26 mmol) 3-[(2-bromo-thiazole-4-carbonyl)-amino]-3-o-tolyl-propionic acid methyl ester are dissolved in 10 ml MeOH, 0.55 ml of 1N NaOH solution (2.1 Eq NaOH) are added and the resulting mixture is stirred for 1 h. 10 ml of water are added and the pH of the resulting mixture is adjusted to 5.5 by addition of 10% HCl and the MeOH removed in vacuo. The remaining aqueous phase is extracted three times with 10 ml of CH2Cl2, the organic layer is collected, dried over Na2SO4 and the solvent removed in vacuo to deliver 3-[(2-Bromo-thiazole-4-carbonyl)-amino]-3-o-tolyl-propionic acid in yields below 90%

Workup

  1. customthe MeOH removed in vacuo
  2. extractionThe remaining aqueous phase is extracted three times with 10 ml of CH2Cl2
  3. customthe organic layer is collected
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-09766dde63e641298ddf94ca3bdd7bcb
Source dataset
uspto-grants-2015_11
Patent number
US09174952B2

Reaction notes

Loading…