Lithium Hydroxide → 1-{3-[2-(2-Fluoro-5-methyl-phenyl)-ethoxy]-4-methoxy-benzoylamino}-cycloheptanecarboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1([NH:12][C:13](=[O:33])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Li+]>O1CCOCC1>[F:32][C:26]1[CH:27]=[CH:28][C:29]([CH3:31])=[CH:30][C:25]=1[CH2:24][CH2:23][O:22][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[O:20][CH3:21])[C:13]([NH:12][C:5]1([C:3]([OH:4])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:33]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The compound of step 3 (160 mg, 0.35 mmol) was dissolved in dioxane (1.8 ml). 1 M aqueous lithium hydroxide (1.8 ml) was added, the mixture was stirred at 60° C. for 30 min, cooled, and partitioned between 2 N hydrochloric acid and EA. The aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate, filtered and evaporated to dryness. The residue was stirred in ether and the solid material which formed was filtered and dried in vacuo to yield the title compound (126 mg).
Workup
- temperaturecooled
- custompartitioned between 2 N hydrochloric acid and EA
- extractionThe aqueous phase was extracted with EA
- dry with materialthe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness
- stirringThe residue was stirred in ether
- customthe solid material which formed
- filtrationwas filtered
- customdried in vacuo
Sources & evidence
- ORD record
- ord-d5743a73c6b745a8ad752827f9db5143
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618304B2
Reaction notes
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