Hydrochloric Acid → HCID 19818635, compound

HRID 652322Notes

Reaction equation

HRID 652322 reaction equation
[OH-].[Na+].[C:3]([C:6]1[CH:31]=[CH:30][C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:27])[C:23]([O:25]C)=[O:24])=[CH:17][C:16]=2[O:28][CH3:29])=[C:8]([CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:7]=1[OH:38])(=[O:5])[CH3:4].Cl>CO>[C:3]([C:6]1[CH:31]=[CH:30][C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:27])[C:23]([OH:25])=[O:24])=[CH:17][C:16]=2[O:28][CH3:29])=[C:8]([CH2:32][CH2:33][C:34]([F:36])([F:35])[F:37])[C:7]=1[OH:38])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19818646HCID 19818646, compound

Product 1

HCID 19818635HCID 19818635, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

18 ml of N sodium hydroxide solution are added to a solution of 7.95 g of methyl N-{{4-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-3-methoxy-phenyl}}-oxamate in 100 ml of methanol and the mixture is refluxed for 1 hour. The hot solution is then poured into 200 ml of 0.1N hydrochloric acid. The product which has precipitated out is filtered off, washed with water and dired over phosphorus pentoxide in a drying cabinet. The N-{{4-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-3-methoxy-phenyl}}-oxamic acid thus obtained is dissolved hot again in 100 ml of methanol, and one equivalent of triethanolamine in 10 ml of methanol is added. After addition of 400 ml of ether, crystallisation starts. The triethanolammonium salt of N-{{4-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-3-methoxy-phenyl}}-oxamic acid is thus obtained.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. customThe product which has precipitated out
  3. filtrationis filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-fccdd9e915f74baa8cffb5f78f832e5e
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

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