Water → 2-(2-Cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid

HRID 1394109Notes

Reaction equation

HRID 1394109 reaction equation
O.[CH:2]1([CH2:8][C:9]([NH:11][C:12]2[S:13][C:14]3[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([O:23]CC)=[O:22])[C:15]=3[N:16]=2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+]>CO>[CH:2]1([CH2:8][C:9]([NH:11][C:12]2[S:13][C:14]3[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([OH:23])=[O:22])[C:15]=3[N:16]=2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59681856Ethyl 2-(2-cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate

Product 1

HCID 596818682-(2-Cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (20 mL) and MeOH (80 mL) were added to ethyl 2-(2-cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate (F) (4.9 g, 14 mmol) and NaOH (5.6 g, 0.14 mol), and the resultant mixture was stirred at RT under a blanket of nitrogen as inert gas until completion of the reaction. Following removal of MeOH, 2N hydrochloric acid solution in water (250 mL) and DCM (250 mL) was added. The phases were separated, and the aqueous phase was extracted a number of times with DCM. Following drying of the combined organic phases over Na2SO4 and filtration, there was obtained the product 2-(2-cyclohexylacetylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid (G) in a yield of 3.9 g (corresponding to 87% of theory).

Workup

  1. customremoval of MeOH, 2N hydrochloric acid solution in water (250 mL) and DCM (250 mL)
  2. additionwas added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted a number of times with DCM
  5. dry with materialFollowing drying of the combined organic phases over Na2SO4 and filtration

Sources & evidence

ORD record
ord-7b64f1cff8c7496689aaf0856ca094e8
Source dataset
uspto-grants-2008_03
Patent number
US07348347B2

Reaction notes

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