Trifluoroacetic acid → HCID 178504906, compound

HRID 1257725Notes

Reaction equation

HRID 1257725 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>C(Cl)Cl>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[CH3:17][S:14]([C@H:11]1[CH2:12][CH2:13][C@H:8]([NH2:7])[CH2:9][CH2:10]1)(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454083HCID 178454083, compound

Product 1

HCID 178504906HCID 178504906, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of trans (4-methanesulfonyl-cyclohexyl)-carbamic acid tert-butyl ester (0.40 g, 1.40 mmol) in DCM (5 mL) was treated with trifluoroacetic acid (5 mL) and the mixture was stirred at ambient temperature for 30 minutes then concentrated under vacuum. The residue was azeotroped with toluene (×2) and the resulting oil was triturated (diethyl ether) to provide a solid which was washed with ether and dried to give 386 mg (93%) of trans 4-methanesulfonyl-cyclohexylamine trifluoroacetic acid salt as a white solid. 1H NMR (400 MHz, DMSO) δ: 7.86 (s, 3H), 3.11-2.98 (m, 2H), 2.92 (s, 3H), 2.18-2.02 (m, 4H), 1.56-1.43 (m, 2H), 1.43-1.28 (t, 2H).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was azeotroped with toluene (×2)
  3. customthe resulting oil was triturated (diethyl ether)
  4. customto provide a solid which
  5. washwas washed with ether
  6. customdried

Sources & evidence

ORD record
ord-7d17196c44964e14bc31803dfaff1eec
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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