Trifluoroacetic acid → HCID 58495657, compound

HRID 1190986Notes

Reaction equation

HRID 1190986 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]\[CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=1)=O)(C)(C)C>C(Cl)Cl>[CH:25]1(/[CH:24]=[CH:23]\[C:20]2[CH:19]=[CH:18][C:17]([CH2:16][NH2:15])=[CH:22][CH:21]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58495496HCID 58495496, compound

Product 1

HCID 58495657HCID 58495657, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (1 mL) to a solution of (Z)—N-(tert-butoxycarbonyl)-4-(2-cyclohexylvinyl)-benzylamine (0.49 g, 1.5 mmol) in DCM (10 mL). Stir the mixture at room temperature for 2 h, concentrate in vacuo and purify the residue by SCX chromatography to obtain the title compound (0.3 g, 87%, estimate 10% of alkane present). Use this material in the next step without additional purification. MS (ES+) m/z: 199.3 (M-NH3+H)+.

Workup

  1. concentrationconcentrate in vacuo
  2. custompurify the residue by SCX chromatography

Sources & evidence

ORD record
ord-369bc53151154dbf9b9f5d0b98b2fb4a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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