Water → HCID 59681877, compound

HRID 1394111Notes

Reaction equation

HRID 1394111 reaction equation
O.[C:2]1([CH:8]([CH3:26])[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])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[C:2]1([CH:8]([CH3:26])[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])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59681855HCID 59681855, compound

Product 1

HCID 59681877HCID 59681877, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (20 mL) and MeOH (80 mL) were added to ethyl 2-(2-phenylpropionylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylate (R) (4.95 g, 13.8 mmol) and NaOH (5.52 g, 0.138 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) were added. The phases were separated, and the aqueous phase was extracted a number of times with DCM (a total of 200 mL). Following drying of the combined organic phases over Na2SO4 and filtration, there was obtained the product 2-(2-phenylpropionylamino)-4,5,6,7-tetrahydrobenzthiazol-4-carboxylic acid (S) in a yield of 4.6 g (corresponding to 100% of theory).

Workup

  1. customremoval of MeOH, 2N hydrochloric acid solution in water (250 mL) and DCM (250 mL)
  2. additionwere added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted a number of times with DCM (a total of 200 mL)
  5. dry with materialFollowing drying of the combined organic phases over Na2SO4 and filtration

Sources & evidence

ORD record
ord-14866fa85f724e65830623e9f3f62f9d
Source dataset
uspto-grants-2008_03
Patent number
US07348347B2

Reaction notes

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