Hydrochloric Acid → N-[2-(4-Carboxymethoxyphenyl)-1-methylethyl]-N-(2-hydroxyethyl)-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

HRID 1587947Notes

Reaction equation

HRID 1587947 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]([CH2:29][CH2:30][OH:31])[CH2:17][CH:18]([OH:28])[C:19]2[N:20]=[C:21]([C:24]([F:27])([F:26])[F:25])[S:22][CH:23]=2)[CH3:15])=[CH:9][CH:8]=1)([O:3]C)=[O:2].[OH-].[Na+].Cl>CO>[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]([CH2:29][CH2:30][OH:31])[CH2:17][CH:18]([OH:28])[C:19]2[N:20]=[C:21]([C:24]([F:27])([F:25])[F:26])[S:22][CH:23]=2)[CH3:15])=[CH:9][CH:8]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19974326HCID 19974326, compound

Product 1

HCID 19974169N-[2-(4-Carboxymethoxyphenyl)-1-methylethyl]-N-(2-hydroxyethyl)-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared by analogy to Example 16 by reaction of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-N-(2-hydroxyethyl)-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine in methanol with 1N sodium hydroxide solution. After the mixture has been neutralised with 1N hydrochloric acid it is evaporated to dryness, treated with 10 ml of ethanol, and the inorganic residues are removed by filtration. The ethanol phase is diluted with 60 ml of methylene chloride and again filtered. The mother liquor is evaporated to dryness, and the residue is triturated with ether and filtered off with suction.

Workup

  1. customis evaporated to dryness
  2. additiontreated with 10 ml of ethanol
  3. customthe inorganic residues are removed by filtration
  4. additionThe ethanol phase is diluted with 60 ml of methylene chloride
  5. filtrationagain filtered
  6. customThe mother liquor is evaporated to dryness
  7. customthe residue is triturated with ether
  8. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-2ecd9d5eecc84deb90dfd37619bd9057
Source dataset
uspto-grants-1993_06
Patent number
US05219852

Reaction notes

Loading…