HCID 57509717, compound → HCID 57510026, compound

HRID 624173Notes

Reaction equation

HRID 624173 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)=[O:18])=[CH:12][CH:11]=2)=[O:9])[CH2:2]1>CO>[O:1]1[CH2:5][CH2:4][C@H:3]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([N:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)=[O:18])=[CH:14][CH:15]=2)=[O:9])[CH2:2]1

Participants

3

Reactant 1

HCID 57509717HCID 57509717, compound

Product 1

HCID 57510026HCID 57510026, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A racemic mixture of N-(4-{[tetrahydrofuran-3-ylmethyl]carbamoyl}phenyl)-1,3-dihydro-2H-isoindole-2-carboxamide (250 mg) was dissolved in methanol and separated using SCF-LC with a ChiralPak AD-H 21×250 mm column to provide N-(4-{[(3R)-tetrahydrofuran-3-ylmethyl]carbamoyl}phenyl)-1,3-dihydro-2H-isoindole-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.57 (s, 1H), 8.38 (t, J=5.7 Hz, 1H), 7.75-7.79 (m, 2H), 7.64-7.69 (m, 2H), 7.30-7.39 (m, 4H), 4.78-4.79 (bs, 4H), 3.57-3.78 (m, 3H), 3.48 (dd, J=8.5, 5.3 Hz, 1H), 3.13-3.29 (m, 2H), 2.40-2.50 (m, 1H), 1.87-2.07 (m, 1H), 1.54-1.66 (m, 1H); MS (ESI(+)) m/e 366 (M+H)+.

Workup

  1. customseparated

Sources & evidence

ORD record
ord-911299a139fb4da8845d191d8eaa7f59
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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