1-[(Benzylamino)methyl]cyclohexan-1-OL → N4-benzyl-N4-[(1-hydroxycyclohexyl)methyl]-N1-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(4-thiazolylmethyl)butanediamide

Participants

Reaction Steps

4{[1(S)-(Cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino}-4-oxo-3(R)-(4-thiazolylmethyl)-butanoic acid (61 mg, 0.14 mmol, described in example 2, section D) was coupled with 1-{[(phenylmethyl)amino]methyl}cyclohexanol (31 mg, 0.14 mmol, described in example 1, section D) according to the procedure described in example 3 to give the title compound (41 mg, 17%); 1H NMR (400 MHz, DMSO-d6) (2.2:1 mixture of rotamers) δ9.00 and 8.95 (d, J=1.8 Hz, 1H), 7.76 and 7.71 (d, J=8.9 Hz, 1H), 7.36-7.20 (m,4H), 7.15 and 7.10 (d, J=7.2 Hz,2H), 4.77 (broad s,2H), 4.62-4.58 (m,2H), 4.43 and 4.34 (s,1H), 4.13-4.02 (m,1H), 3.17 (d, J=13.8 Hz, 1H), 3.09-2.76 (m,5H), 2.62 (dd, J1 =8.1 Hz, J2 =16.5 Hz, 1H), 2.32 (dd, J1 =5.4 Hz, J2 2 =16.1 Hz, 1H), 1.68-1.25 (m,21H), 1.22-1.03 (m,6H), 0.85 and 0.84 (d, J=6.6 Hz, 3H), 0.73 (t, J=5.4 Hz,3H); FAB mass spectrum , m/z: 642 (M+H)+.

Provenance & Evidence