Hydrochloric Acid → HCID 11576980, compound

HRID 1822142Notes

Reaction equation

HRID 1822142 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[O:11][C:12]([CH3:35])=[C:13]([CH2:15][N:16]([CH2:33][CH3:34])[C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:14]=2)[CH:5]=1.[Li+].[OH-].Cl.CCOCC>C1COCC1.O>[CH2:33]([N:16]([CH2:15][C:13]1[N:14]=[C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:36])=[O:2])[O:11][C:12]=1[CH3:35])[C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:30])([F:31])[F:29])=[CH:19][CH:18]=1)[CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 11569845HCID 11569845, compound

Product 1

HCID 11576980HCID 11576980, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 92 mg (0.18 mmol) of 3-[4-({ethyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-amino}-methyl)-5-methyl-oxazol-2-yl]-benzoic acid methyl ester (example 30.2) in 1 mL of THF was treated with 1 mL of 1M aqueous LiOH and stirred at RT for 1 h. The mixture was acidified to pH 4-5 with aqueous HCl and distributed between Et2O and H2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 79 mg (88%) of 3-[4-({ethyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenyl]-amino}-methyl)-5-methyl-oxazol-2-yl]-benzoic acid, light yellow solid, MS: 503 (MH+).

Workup

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customevaporated

Sources & evidence

ORD record
ord-bb193b50068d4f4bb581fe8a0d7161f4
Source dataset
uspto-grants-2009_10
Patent number
US07608721B2

Reaction notes

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