Hydrochloric Acid → Tetrahydro-4-[[[1-[[4-(trifluoromethyl)phenyl]methoxy]-2-naphthalenyl]carbonyl]amino]-2H-thiopyran-4-carboxylic acid

HRID 1039109Notes

Reaction equation

HRID 1039109 reaction equation
C[O:2][C:3]([C:5]1([NH:11][C:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[O:13])[CH2:10][CH2:9][S:8][CH2:7][CH2:6]1)=[O:4].Cl>C1COCC1.[OH-].[Na+].CO>[F:34][C:32]([F:33])([F:35])[C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:22]=[CH:23][C:14]=2[C:12]([NH:11][C:5]2([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][S:8][CH2:9][CH2:10]2)=[O:13])=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68840611HCID 68840611, compound

Product 1

HCID 57831237Tetrahydro-4-[[[1-[[4-(trifluoromethyl)phenyl]methoxy]-2-naphthalenyl]carbonyl]amino]-2H-thiopyran-4-carboxylic acidYield 93.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

126 mg 4-{[1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-tetrahydro-thiopyran-4-carboxylic acid methyl ester in 2.5 ml THF, 0.25 ml 2 M sodium hydroxide and 0.25 ml methanol were reacted at room temperature for 16 h. The reaction was then acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate, and concentrated to yield 115 mg of 4-{[1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-tetrahydro-thiopyran-4-carboxylic acid.

Workup

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d62c2441835c4113a2db569e83bc7dfc
Source dataset
uspto-grants-2013_10
Patent number
US08552033B2

Reaction notes

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