Lithium Hydroxide → HCID 70878224, compound

HRID 1253770Notes

Reaction equation

HRID 1253770 reaction equation
C([O:3][C:4](=[O:36])[C:5]([CH3:35])([CH3:34])[CH2:6][C:7]#[C:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([CH3:20])[C:16]=2[NH:21][C:22]([O:24][CH:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[CH3:26])=[O:23])=[CH:11][CH:10]=1)C.[OH-].[Li+]>CO.O>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH:25]([O:24][C:22]([NH:21][C:16]1[C:17]([CH3:20])=[N:18][O:19][C:15]=1[C:12]1[CH:11]=[CH:10][C:9]([C:8]#[C:7][CH2:6][C:5]([CH3:35])([CH3:34])[C:4]([OH:36])=[O:3])=[CH:14][CH:13]=1)=[O:23])[CH3:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 70878236HCID 70878236, compound

Product 1

HCID 70878224HCID 70878224, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 5-(4-{4-[1-(2-chloro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-phenyl)-2,2-dimethyl-pent-4-ynoic acid ethyl ester (0.46 mmol) in MeOH and H2O was added lithium hydroxide, and the reaction was stirred at 60° C. overnight. The mixture was acidified and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound. Mass spec. data (M+H)=481.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7c4038fbd04f413dbd2065cbcfeae412
Source dataset
uspto-grants-2013_06
Patent number
US08455499B2

Reaction notes

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