Hydrochloric Acid → HCID 69202507, compound

HRID 2220599Notes

Reaction equation

HRID 2220599 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([OH:27])[C@@H:18]([NH:20]C(=O)C(F)(F)F)[CH3:19])=[CH:13][C:12]=1[NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CO>[NH2:20][C@@H:18]([CH3:19])[C@@H:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[C:12]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:13]=1)[OH:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86611768N-[(1S,2R)-2-(4-Benzyloxy-3-methanesulfonylaminophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

Product 1

HCID 69202507HCID 69202507, compoundYield 810.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5 mol/L aqueous solution of sodium hydroxide (6.3 mL) was added to a solution of N-[(1S,2R)-2-(4-benzyloxy-3-methanesulfonylaminophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide (5.5 g) in methanol (100 mL) at room temperature, and the mixture was heated under reflux for 5.5 hrs. After being cooled to room temperature, 2 mol/L hydrochloric acid (15.7 mL) was added to the mixture. The solvent was evaporated under reduced pressure, and the residue was purified by aminopropyl silica gel column chromatography (eluent: ethanol) to afford the title compound (35 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5.5 hrs
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by aminopropyl silica gel column chromatography (eluent: ethanol)

Sources & evidence

ORD record
ord-2ccc791abe674e1ab3b4f089243339bb
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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