Lithium hydroxide, monohydrate → HCID 178522637, compound

HRID 1035744Notes

Reaction equation

HRID 1035744 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[C:32]([F:34])[CH:33]=1)[CH2:5][C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:30]=[CH:29][C:17]([O:18][CH:19]3[CH2:24][CH2:23][CH:22]([C:25]([O:27]C)=[O:26])[CH2:21][CH2:20]3)=[CH:16][CH:15]=2)=[O:13])=[N:8][N:7]=1.O.[OH-].[Li+]>C1COCC1.CO>[F:34][C:32]1[CH:31]=[C:4]([CH:3]=[C:2]([F:1])[CH:33]=1)[CH2:5][C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:30]=[CH:29][C:17]([O:18][C@@H:19]3[CH2:20][CH2:21][C@H:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]3)=[CH:16][CH:15]=2)=[O:13])=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66739812HCID 66739812, compound

Product 1

HCID 178522637HCID 178522637, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.5 g of methyl 4-{4-[5-(3,5-difluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}-cyclohexanecarboxylate (3.08 mmol, 1 eq.) are dissolved in 20 mL of a 1/1 mixture of THF/methanol. 0.258 g of lithium hydroxide monohydrate (6.15 mmol; 2 eq.) is added with stirring. After 16 hours at room temperature, the reaction medium is evaporated, diluted with water, and aqueous 6% sulfur dioxide solution is added. The precipitate is filtered off and washed with water. The residue is then triturated and filtered in ethyl acetate and ethanol. 1.14 g of cis-4-{4-[5-(3,5-difluorobenzyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}cyclohexanecarboxylic acid are obtained.

Workup

  1. customthe reaction medium is evaporated
  2. additiondiluted with water, and aqueous 6% sulfur dioxide solution
  3. additionis added
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customThe residue is then triturated
  7. filtrationfiltered in ethyl acetate

Sources & evidence

ORD record
ord-210bba31853e44e9a81323de97f403f8
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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