Trifluoroacetic acid → HCID 68898419, compound

HRID 747375Notes

Reaction equation

HRID 747375 reaction equation
[C:1]1([NH:7][C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]2[NH:14]C(OC(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([NH:7][C@@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]2[NH2:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86587219cis-N-phenyl-N'-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine

Product 1

HCID 68898419HCID 68898419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The cis-N-phenyl-N′-(t-butyloxycarbonyl)-cyclohexane-1,2-diamine isomer from above (0.095 g, 0.33 mmol) was dissolved in CH2Cl2 (2 mL) and treated with trifluoroacetic acid (2 mL) and the mixture stirred overnight. The reaction was worked up to afford the title compound (0.069 g) as a pale yellow solid. 1H NMR (CDCl3) 1.28-1.37 (m, 5H), 1.50-1.63 (m, 6H), 3.18 (br s, 1H), 3.42-3.45 (m, 1H), 6.63-6.70 (m, 3H), 7.16 (br t, 2H, J=7.5 Hz).

Sources & evidence

ORD record
ord-602441c145c446cc8a35b4f08deab3df
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Reaction notes

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