Benzyl Alcohol → HCID 59474995, compound

HRID 42546Notes

Reaction equation

HRID 42546 reaction equation
C(OC[N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:16]=[C:17]([CH:44]=[CH:45][CH:46]=2)[C:18]([NH:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][C@@H:22]2[C:26]([N:28]2[CH2:33][CH2:32][C@@:31]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)([OH:34])[C:30]([CH3:43])([CH3:42])[CH2:29]2)=[O:27])=[O:19])=[N:11]1)C1C=CC=CC=1.C(O)C1C=CC=CC=1>CO>[Cl:41][C:38]1[CH:37]=[CH:36][C:35]([C@@:31]2([OH:34])[CH2:32][CH2:33][N:28]([C:26]([C@H:22]3[CH2:23][CH2:24][CH2:25][C@H:21]3[NH:20][C:18](=[O:19])[C:17]3[CH:44]=[CH:45][CH:46]=[C:15]([C:12]4[N:11]=[N:10][NH:14][N:13]=4)[CH:16]=3)=[O:27])[CH2:29][C:30]2([CH3:42])[CH3:43])=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 59474996HCID 59474996, compound

Product 1

HCID 59474995HCID 59474995, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Example 24 was prepared from 3-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)-N-((1R,2S)-2-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine-1-carbonyl)cyclopentyl)benzamide using similar conditions as described in Example 22. MS (ESI+)=523 (M)+. 1H NMR (CD3OD, 500 MHz) (NMR shows several rotamers) (NMR indicates contamination with 0.5 eq. (mol) of benzyl alcohol—chemical shifts for contaminant not reported) δ 8.46 (s, 0.3H), 8.39 (s, 0.7H), 8.24 (d, J=8.0 Hz, 0.3H), 8.20 (d, J=8.0 Hz, 0.7H), 7.97 (d, J=8.3 Hz, 0.3H), 7.91 (d, J=8.3 Hz, 0.7H), 7.73 (t, J=7.8 Hz, 0.3H), 7.67 (t, J=7.7 Hz, 0.7H), 7.45 d, J=8.8 Hz, 1.4H), 7.33 d, J=8.8 Hz, 0.6H), 7.28 (d, J=8.5 Hz, 1.4H), 7.19 (d, J=8.5 Hz, 0.6H), 4.79 (q, J=7.4 Hz, 0.7H), 4.62-4.54 (m, 0.6H), 4.15-4.06 (m, 0.7H), 4.02 (d, J=12.7 Hz, 0.7H), 3.66-3.51 (m, 2.3H), 3.18-3.06 (m, 0.3H), 2.94 (d, J=12.4 Hz, 0.7H), 2.71 (td, J=13.5, 4.7 Hz, 0.7H), 2.49 (td, J=13.3, 4.4 Hz, 0.3H), 2.29-1.80 (m, 5H), 1.76-1.63 (m, 1H), 1.53 (d, J=14.0 Hz, 0.7H), 1.50-1.44 (m, 0.3H), 0.80 (s, 0.8H), 0.77-0.68 (m, 5.2H). [LCMS method: Inj. Vol.=10 uL; Start % B=0; Final % B=100; Gradient Time=2 min; Flow Rate=5 ml/min; Wavelength=220 nm; Solvent A=10% MeOH-90% H2O-0.1% TFA; Solvent B=90% MeOH-10% H2O-0.1% TFA; Column 1=Sunfire S5 C18 4.6×30 mm (2 min grad); Retention Time=1.90 minutes.]

Workup

  1. customδ 8.46 (s, 0.3H), 8.39 (s, 0.7H), 8.24 (d, J=8.0 Hz, 0.3H), 8.20 (d, J=8.0 Hz, 0.7H), 7.97 (d, J=8.3 Hz, 0.3H), 7.91 (d, J=8.3 Hz, 0.7H), 7.73 (t, J=7.8 Hz, 0.3H), 7.67 (t, J=7.7 Hz, 0.7H), 7.45 d, J=8.8 Hz, 1.4H
  2. custom7.33 d, J=8.8 Hz, 0.6H
  3. customGradient Time=2 min
  4. customC18 4.6×30 mm (2 min grad)

Sources & evidence

ORD record
ord-99ea55e0aa5b4eab9aa47f4c3f2c7e18
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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