Tetrahydrofuran → HCID 46843708, compound

HRID 1035698Notes

Reaction equation

HRID 1035698 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:32]=[CH:31][C:19]([O:20][CH:21]3[CH2:26][CH2:25][CH:24]([C:27]([O:29]C)=[O:28])[CH2:23][CH2:22]3)=[CH:18][CH:17]=2)=[O:15])=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.O.[OH-].[Li+]>O>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:32]=[CH:31][C:19]([O:20][CH:21]3[CH2:22][CH2:23][CH:24]([C:27]([OH:29])=[O:28])[CH2:25][CH2:26]3)=[CH:18][CH:17]=2)=[O:15])=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66740015HCID 66740015, compound

Product 1

HCID 46843708HCID 46843708, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

0.128 g of methyl 4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenoxy]cyclohexanecarboxylate (0.28 mmol, 1 eq.) is placed in 2 mL of a mixture of tetrahydrofuran and water at room temperature. 0.024 g of lithium hydroxide monohydrate (0.57 mmol, 2 eq.) in 1 mL of water is added. After stirring for 2 hours at room temperature, the tetrahydrofuran is evaporated off and water is added. The aqueous phase is washed with dichloromethane. The aqueous phase is cooled to a temperature of 4° C. in an ice bath and acidified with 1N hydrochloric acid solution. The solid is filtered off and washed successively with water, with ethanol and then with diethyl ether to give 0.069 g of 4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenoxy]cyclohexanecarboxylic acid.

Workup

  1. customthe tetrahydrofuran is evaporated off
  2. additionwater is added
  3. washThe aqueous phase is washed with dichloromethane
  4. temperatureThe aqueous phase is cooled to a temperature of 4° C. in an ice bath
  5. filtrationThe solid is filtered off
  6. washwashed successively with water, with ethanol

Sources & evidence

ORD record
ord-479e5624ad584e08abab7395b65f711a
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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