Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68674598, compound

HRID 2264173Notes

Reaction equation

[CH2:1]([N:5]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]([O:32]C3CCCCO3)[C:26]=2[CH:39]=1)[C:6]([CH:8]1[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:32][CH:27]1[C:26]2[CH:39]=[C:22]([CH2:21][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]([CH:8]3[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:9]3)=[O:7])[CH:23]=[CH:24][C:25]=2[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 1.91 g (3.5 mmol) of (±)-tert-butyl 2-[(isobutyl {[9-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl]methyl}amino)carbonyl]morpholine-4-carboxylate and 0.088 g (0.35 mmol, 0.1 equiv) of pyridinium p-toluenesulfonate in 25 mL of ethanol was stirred under nitrogen at 55° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (10-50% ethyl acetate in hexanes) to give the product as a solid white foam. MS (m+1)=461.4; H NMR (400 MHz, CDCl3) 7.29 (m, 1H), 7.05 (m, 1H), 6.96 (m, 1H), 4.91 (t, 1H, J 8 Hz), 4.75 (m, 1H), 4.48 (d, 1H, J 16 Hz), 4.18-4.02 (m, 2H), 4.01-3.80 (m, 2H), 3.57-3.38 (m, 2H), 3.21 (m, 1H), 3.10-2.85 (m, 3H), 2.69 (m, 1H), 2.01 (m, 3H), 1.78 (m, 3H), 1.57 (m, 2H, obscured by H2O peak), 1.45 (d, 9H, J 15 Hz), 0.90 (m, 6H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by flash chromatography (10-50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-596239ef334a4f5e9ae1a7422e4c341c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855201B2

Reaction notes

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