HCID 57544846, compound → HCID 67190416, compound

HRID 2355522Notes

Reaction equation

HRID 2355522 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[C:6]([C@:15]([C@@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([NH:31][C@H:32]3[CH2:37][CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33]3)=[O:30])[CH2:24]2)([OH:22])[CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.ClCCl>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[C:6]([C@:15]([C@@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([NH:31][CH:32]3[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]3)=[O:30])[CH2:24]2)([OH:22])[CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 57544846HCID 57544846, compound

Product 1

HCID 67190416HCID 67190416, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(S)-tert-Butyl 3-((R)-3-((S)-1-(6-fluoro-3′-methylbiphenyl-2-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)piperidine-1-carboxylate (20 mg, 0.033 mmol) was dissolved in TFA/dichloromethane (1 mL, 1:3, v/v), stirred 20 min, evaporated, and purified by preparative HPLC to give the (3R)-3-((S)-1-(6-fluoro-3′-methylbiphenyl-2-yl)-1-hydroxy-5-methoxypentyl)-N-(piperidin-3-yl)piperidine-1-carboxamide (9.39 mg) as its TFA salt. 1H NMR (400 MHz, CD3OD): 6 ppm 7.57 (d, J=8.4 Hz, 1H), 7.36-7.20 (m, 3H), 7.04-7.02 (m, 2H), 6.92 (m, 1H), 4.03 (m, 1H), 3.85-3.75 (m, 2H), 3.39-3.32 (m, 3H), 3.29 (s, 3H), 2.86 (m, 1H), 2.71-2.56 (m, 3H), 2.37, 2.35 (two s, 3H, rotamer), 1.99 (m, 2H), 1.88-1.26 (m, 13H), 0.92 (m, 1H). MS m/z 512 (M+H)+.

Workup

  1. customevaporated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a6bb310950ba43999d754493622267a6
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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