Trifluoroacetic acid → HCID 59444251, compound

HRID 1888113Notes

Reaction equation

HRID 1888113 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:34])[CH2:13][CH2:12][N:11]([C:14](=[O:31])[CH2:15][C@H:16]([NH:18][C:19]([C:21]3[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=3)[C:24]([O:26]C)=[O:25])=[O:20])[CH3:17])[CH2:10][C:9]2([CH3:33])[CH3:32])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>O.CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:34])[CH2:13][CH2:12][N:11]([C:14](=[O:31])[CH2:15][C@H:16]([NH:18][C:19]([C:21]3[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=3)[C:24]([OH:26])=[O:25])=[O:20])[CH3:17])[CH2:10][C:9]2([CH3:33])[CH3:32])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59444229HCID 59444229, compound

Product 1

HCID 59444251HCID 59444251, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent2×

Procedure

Example 8 was prepared from methyl 3-((R)-4-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-4-oxobutan-2-ylcarbamoyl)benzoate using the conditions described in Example 6. MS (ESI+)=473.2 (M+H)+. 1H NMR (CD3OD, 500 MHz) (NMR shows several rotamers) δ ppm 8.54 (t, J=1.6 Hz, 0.6 H), 8.46 (t, J=1.6 Hz, 0.4 H), 8.22 (d, J=7.7 Hz, 0.6 H), 8.17 (d, J=7.7 Hz, 0.4 H), 8.08 (d, J=8.2 Hz, 0.6 H), 8.02 (d, J=7.7 Hz, 0.4 H), 7.61 (t, J=7.7 Hz, 0.6 H), 7.57 (t, J=7.7 Hz, 0.4 H), 7.47 (d, J=8.8 Hz, 0.8 H), 7.32-7.25 (m, 2 H), 7.23 (d, J=8.3 Hz, 1.2 H), 4.64-4.46 (m, 1.4 H), 4.10 (dt, J=13.2, 2.5 Hz, 0.6 H), 4.04 (dd, J=12.6, 2.2 Hz, 0.6 H), 3.67-3.53 (m, 1.4 H), 3.17-3.03 (m, 1.6 H), 2.97 (dd, J=14.9, 6.1 Hz, 0.4 H), 2.67-2.46 (m, 2 H), 1.57-1.47 (m, 1 H), 1.40 (d, J=6.6 Hz, 1.8 H), 1.34 (d, J=6.6 Hz, 1.2 H), 0.83 (s, 1.2 H), 0.82 (s, 1.2 H), 0.76 (s, 1.8 H), 0.66 (s, 1.8 H); HPLC Method: Inj. Vol.=5 uL, Start % B=10, 12 Min. 100%, 15 Min. 100%, Flow Rate=1 ml/min, Wavelength 1=220, Wavelength 2=254, Solvent A=0.05% TFA in H2O:MeCN (95:5), Solvent B=0.05% TFA in H2O:MeCN (5:95), Col-1: Sunfire C18 3.5 um, 4.6×150 mm; Retention Time=10.92 min., Col-2: Xbridge Phenyl 3.5 um, 4.6×150 mm; Retention Time=10.45 min.

Sources & evidence

ORD record
ord-08a9e7e76dd645da9716ed62cdcf7a09
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

Loading…