Triethylamine → HCID 89610545, compound

HRID 1507689Notes

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:24][CH2:25][CH3:26])=[O:23])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([O:37]CC)=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:42]([N:44]([CH2:47][CH3:48])[CH2:45][CH3:46])[CH3:43]>C1COCC1.CCO.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:24][CH2:25][CH3:26])=[O:23])[N:11]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:10]=1[C:35]([O-:37])=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:42]([NH+:44]([CH2:47][CH3:48])[CH2:45][CH3:46])[CH3:43]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of diethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (1) (39.6 g, 74.8 mmol) in THF/EtOH (300/50 mL) was added NaOH (3.07 g, 77 mmol) as a solution in water (20 mL). The reaction was stirred at 50° C. for 16 h. Triethylamine was added (30 mL, 215 mmol) and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography (50% isohexane:DCM (+2% Et3N), then 20% MeOH/EtOAc (+2% Et3N)) to afford triethylammonium 3,4-bis(benzyloxy)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (5) (39.3 g, 83%) as a yellow oil: m/z 502 (M+H)+ (ES+); 500 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.26 (m, 10H), 7.11-7.05 (m, 2H), 6.92-6.83 (m, 2H), 5.09 (s, 2H), 5.06 (s, 2H), 3.95 (q, J=7.1 Hz, 2H), 3.79 (s, 3H), 2.85-2.62 (m, 6H), 1.08-0.92 (m, 12H).

Workup

customthe volatiles were removed in vacuo
customThe residue was purified by silica gel chromatography (50% isohexane

Sources & evidence

ORD record: ord-1d1a5f0a8be3461ab896d5afb2471e6f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221756B2

Reaction notes

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