1,4-Dioxane → HCID 89610490, compound

HRID 1507716Notes

Reaction equation

HRID 1507716 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])=[C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:10]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1>Cl>[CH2:1]([O:8][C:9]1[C:13]([O:14][CH2:15][C:16]([OH:18])=[O:17])=[C:12]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:11]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[C:10]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 89610318HCID 89610318, compound

Product 1

HCID 89610490HCID 89610490, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Diethyl 3-(benzyloxy)-4-(2-(tert-butoxy)-2-oxoethoxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (UL2-028) (250 mg, 0.45 mmol) was dissolved in 4 M HCl in dioxane (2.5 mL, 10.0 mmol), and the reaction mixture was stirred at RT for 2 h, volatiles were removed in vacuo and the product was azeotroped with toluene (2×5 mL) to afford 2-((4-(benzyloxy)-2,5-bis(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrol-3-yl)oxy)acetic acid (24) (216 mg, 87%) as a yellow oil: m/z 498 (M+H)+ (ES+); 496 (M−H)− (ES−).

Workup

  1. customvolatiles were removed in vacuo
  2. customthe product was azeotroped with toluene (2×5 mL)

Sources & evidence

ORD record
ord-5278f93234174de581f06c606345df46
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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