Lithium hydroxide, monohydrate → HCID 178522632, compound

HRID 1035716Notes

Reaction equation

HRID 1035716 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([NH:13][C:14]([C:16]3[CH:32]=[CH:31][C:19]([O:20][C@@H:21]4[CH2:26][CH2:25][C@H:24]([C:27]([O:29]C)=[O:28])[CH2:23][CH2:22]4)=[CH:18][CH:17]=3)=[O:15])=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.O.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([NH:13][C:14]([C:16]3[CH:32]=[CH:31][C:19]([O:20][C@@H:21]4[CH2:22][CH2:23][C@H:24]([C:27]([OH:29])=[O:28])[CH2:25][CH2:26]4)=[CH:18][CH:17]=3)=[O:15])=[N:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178501266HCID 178501266, compound

Product 1

HCID 178522632HCID 178522632, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

150 mg of methyl cis-4-{4-[5-(3-chlorophenyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}-cyclohexanecarboxylate (0.32 mmol, 1 eq.) is placed in 1 mL of tetrahydrofuran. 27 mg of lithium hydroxide monohydrate (0.64 mmol, 2 eq.) dissolved in 1 mL are added and stirring is continued for 18 hours. The reaction medium is diluted with water, washed with ethyl acetate and acidified with aqueous 6% sulfur dioxide solution. The solid obtained is filtered off by suction and washed successively with water, ethanol and diethyl ether. 96 mg of cis-4-{4-[5-(3-chlorophenyl)[1.3.4]thiadiazol-2-ylcarbamoyl]-phenoxy}cyclohexanecarboxylic acid are obtained.

Workup

  1. additionare added
  2. washwashed with ethyl acetate
  3. customThe solid obtained
  4. filtrationis filtered off by suction
  5. washwashed successively with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-6b103727d446442ab4897fec6936ddef
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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