Hydrochloric Acid → N-((1RS,2SR)-2-Amino-cyclopentyl)-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide

HRID 659193Notes

Reaction equation

HRID 659193 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[NH:13][C:14](=[O:29])[C:15]1[C:20]([S:21][CH3:22])=[CH:19][C:18]([C:23]([F:26])([F:25])[F:24])=[CH:17][C:16]=1[O:27][CH3:28])(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[NH:13][C:14](=[O:29])[C:15]1[C:20]([S:21][CH3:22])=[CH:19][C:18]([C:23]([F:25])([F:26])[F:24])=[CH:17][C:16]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66682567[(1SR,2RS)-2-(2-Methoxy-6-methylsulfanyl-4-trifluoromethyl-benzoylamino)-cyclopentyl]-carbamic acid tert-butyl ester2×

Product 1

HCID 66681196N-((1RS,2SR)-2-Amino-cyclopentyl)-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(1SR,2RS)-2-(2-Methoxy-6-methylsulfanyl-4-trifluoromethyl-benzoylamino)-cyclopentyl]-carbamic acid tert-butyl Ester (intermediate N, 0.2 g, 0.45 mmol) was dissolved in 2 mL methanol. Hydrochloric acid (4M in dioxane, 0.56 mL, 2.2 mmol) was added and the reaction mixture was stirred at room temperature for 4 h. The mixture was poured into 2N sodium carbonate solution and was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product was used without any further purification, white solid (147 mg, 94%), MS: m/e=349.2 [(M+H)+].

Workup

  1. extractionwas extracted three times with ethyl acetate
  2. customThe combined organic phases were dried on sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was used without any further purification, white solid (147 mg, 94%), MS

Sources & evidence

ORD record
ord-e2b99dab817a45d7b399f5d9c40ced4f
Source dataset
uspto-grants-2011_12
Patent number
US08080541B2

Reaction notes

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