Lithium hydroxide, monohydrate → HCID 178522635, compound

HRID 1035703Notes

Reaction equation

HRID 1035703 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([C:29]([O:31]CC)=[O:30])[CH2:25][CH2:24]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.O.[OH-].[Li+]>O1CCCC1.O>[CH2:1]([C:8]1[S:12][C:11]([NH:13][C:14]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([C:29]([OH:31])=[O:30])[CH2:25][CH2:24]3)=[CH:20][CH:21]=2)=[O:15])=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178472423HCID 178472423, compound

Product 1

HCID 178522635HCID 178522635, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg of ethyl trans-4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenylamino]cyclohexanecarboxylate (0.11 mmol, 1 eq.) are placed in 1 mL of tetrahydrofuran. 9 mg of lithium hydroxide monohydrate (0.22 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. 13 mg of trans-4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenylamino]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-d109da6f69044aec81eec30916f67131
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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