Hydrochloric Acid → HCID 11613217, compound

HRID 346857Notes

Reaction equation

HRID 346857 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[O:11][C:12]([CH3:36])=[C:13]([CH2:15][N:16]3[C:24]4[C:19](=[CH:20][C:21]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:22][CH:23]=4)[CH2:18][CH:17]3[CH3:35])[N:14]=2)[CH:5]=1.[Li+].[OH-].Cl>CCOCC>[CH3:36][C:12]1[O:11][C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:37])=[O:2])=[N:14][C:13]=1[CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:27])([F:28])[F:29])=[CH:22][CH:23]=2)[CH2:18][CH:17]1[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11613417HCID 11613417, compound

Product 1

HCID 11613217HCID 11613217, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 50 mg (0.095 mmol) of 3-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-oxazol-2-yl}-benzoic acid methyl ester (example 90) was added 1 mL of a 1M aqueous LiOH-solution and the mixture stirred at RT for 1 h. After acidification with aqueous HCl to pH of ca 3–4, Et2O was added, the phases were separated and the aqueous one extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 49 mg (quantitative) of 3-{5-methyl-4-[2-methyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-ylmethyl]-oxazol-2-yl}-benzoic acid, off-white solid, MS: 513, (M−H)−.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous one extracted with Et2O
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-af84dda190d44041a366b61c953d81c4
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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