Trifluoroacetic acid → HCID 59444258, compound

HRID 1888130Notes

Reaction equation

HRID 1888130 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([OH:17])[CH2:14][CH2:13][NH:12][CH2:11][C@:10]2([CH3:16])[OH:15])=[CH:5][CH:4]=1.[CH:18]1([C:23]([NH:25][C:26]([CH3:32])([CH3:31])[CH2:27][C:28](O)=[O:29])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]1.C(O)(C(F)(F)F)=O.C(#N)C.O.C(O)(C(F)(F)F)=O>O.CC#N>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([OH:17])[CH2:14][CH2:13][N:12]([C:28](=[O:29])[CH2:27][C:26]([NH:25][C:23]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:24])([CH3:32])[CH3:31])[CH2:11][C@@:10]2([OH:15])[CH3:16])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 22145617Water TFA acetonitrileHCID 64672872HCID 64672872, compoundHCID 68478946HCID 68478946, compound

Product 1

HCID 59444258HCID 59444258, compound

Reagents, catalysts & solvents 1

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

Procedure

Example 96 was prepared from (3S,4S)-4-(4-chlorophenyl)-3-methylpiperidine-3,4-diol hydrochloride and 3-(cyclopentanecarboxamido)-3-methylbutanoic acid using the procedure described in Example 93, step 6. MS (ESI+)=437.3 (M+H)+. 1H NMR (CD3OD, 500 MHz) (NMR shows several rotamers) δ ppm 7.55-7.50 (m, 2 H), 7.31 (d, J=8.5 Hz, 2 H), 4.53 (dd, J=10.7, 1.9 Hz, 0.4 H), 4.28 (dt, J=12.4, 0.8 Hz, 0.6 H), 4.04 (dd, J=13.2, 2.7 Hz, 0.6 H), 3.69 (dd, J=13.1, 2.3 Hz, 0.4 H), 3.59-3.52 (m, 1 H), 3.24 (d, J=14.6 Hz, 0.4 H), 3.09 (d, J=12.1 Hz, 1 H), 2.65-2.49 (m, 2 H), 2.42 (td, J=13.3, 4.7 Hz, 0.4 H), 1.89-1.53 (m, 10 H), 1.47-1.40 (m, 6 H), 0.93 (s, 1.1 H), 0.92-0.86 (m, 2.4 H); HPLC Method: Inj. Vol.=5 uL, Start % B=10, 12 Min. 100%, 15 Min. 100%, Flow Rate=2 mL/min (1 mL/min on each column), Wavelength 1=220 nm, Wavelength 2=254 nm, Solvent Pair=TFA−ACN/H2O, 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=8.27 minutes, Col-2: Xbridge Phenyl 3.5 um, 4.6×150 mm; Retention Time=7.76 minutes.

Sources & evidence

ORD record
ord-35b277db4a8a4bfaaceca4507d8985dc
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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