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

HRID 1950906Notes

Reaction equation

HRID 1950906 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-6f0caaf5601f4ca7903e94a527e024e3
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

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