4-[(4-Methoxyphenyl)methoxy]aniline → Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate

HRID 1507733Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33]CC3C=CC(OC)=CC=3)=[CH:29][CH:28]=2)[C:10]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(COC2C=CC(N)=CC=2)=CC=1>CC(O)=O>[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)[C:10]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-((4-methoxybenzyl)oxy)phenyl)-1H-pyrrole-2-carboxylate (35) [prepared using the same procedure as Example B except 4-((4-methoxybenzyl)oxy)aniline used in step (i)] (46 mg, 0.07 mmol) in AcOH (5 mL) was stirred at 105° C. for 18 h. The volatiles were removed in vacuo and the residue was purified by silica gel chromatography (4 g, 0-10% MeOH in DCM) to afford ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate (36) (35 mg, 91%) as a yellow solid: m/z 515 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 9.63 (1H, s), 7.47-7.42 (m, 2H), 7.41-7.29 (m, 8H), 6.99-6.91 (m, 2H), 6.73-6.66 (m, 2H), 5.10 (s, 2H), 4.95 (s, 2H), 3.99 (q, J=7.1 Hz, 2H), 2.69 (s, 3H), 2.67 (s, 3H), 1.00 (t, J=7.1 Hz, 3H).

Workup

customThe volatiles were removed in vacuo
customthe residue was purified by silica gel chromatography (4 g, 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-802a5c4751674586b5f8519e13c990f5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221756B2

Reaction notes

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