Hydrochloric Acid → HCID 178522638, compound

HRID 1035729Notes

Reaction equation

HRID 1035729 reaction equation
[CH:1]1([O:6][CH2:7][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)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].Cl>C1COCC1.O>[CH:1]1([O:6][CH2:7][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]([OH:29])=[O:28])[CH2:23][CH2:22]4)=[CH:18][CH:17]=3)=[O:15])=[N:10][N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178501269HCID 178501269, compound

Product 1

HCID 178522638HCID 178522638, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.446 g of methyl cis-4-[4-(5-cyclopentyloxymethyl[1.3.4]thiadiazol-2-ylcarbamoyl)-phenoxy]cyclohexanecarboxylate (0.97 mmol, 1 eq.) is placed in 10 mL of THF with stirring, at room temperature, 0.111 g of lithium hydroxide monohydrate (2.64 mmol, 2.7 eq.) dissolved in 10 mL of water is added and the mixture is stirred for 36 hours and left to stand for 48 hours. Aqueous 1N hydrochloric acid solution is then added to acidic pH. The precipitate formed is filtered off and washed with water and with ethanol. 0.320 g of cis-4-[4-(5-cyclopentyloxymethyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenoxy]-cyclohexanecarboxylic acid is obtained.

Workup

  1. additionis added
  2. stirringthe mixture is stirred for 36 hours
  3. waitleft
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water and with ethanol

Sources & evidence

ORD record
ord-16f07a38b51b47029e9516f86c35218b
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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