Acetic Anhydride → HCID 89616791, compound

HRID 1507706Notes

Reaction equation

[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:7]([OH:23])[C:6]=1[OH:24])=[O:4].[C:26](OC(=O)C)(=[O:28])[CH3:27].[CH3:33][C:34]([O-])=[O:35].[Na+]>CCOCC>[C:26]([O:24][C:6]1[C:7]([O:23][C:34](=[O:35])[CH3:33])=[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:5]=1[C:3](=[O:4])[N:2]([CH3:1])[CH3:25])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-012) (120 mg, 0.35 mmol) in acetic anhydride (1 mL, 10.6 mmol) was added NaOAc (90 mg, 1.06 mmol), the suspension was stirred at 100° C. for 2 h. The reaction mixture was partitioned between DCM (25 mL) and iced water (25 mL), dried (MgSO4), filtered and volatiles removed in vacuo to afford a colourless oil. Trituration of the colourless oil from Et2O gave 2-(dimethylcarbamoyl)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl diacetate (UL1-044) (80 mg, 52%) as a white solid: m/z 433 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.27-7.11 (2H, m), 7.00-6.88 (2H, m), 4.00 (q, J=7.1 Hz, 2H), 3.79 (s, 3H), 2.79 (s, 3H), 2.71 (s, 3H), 2.26 (s, 6H) 1.05 (t, J=7.1 Hz, 3H).

Workup

customThe reaction mixture was partitioned between DCM (25 mL) and iced water (25 mL)
dry with materialdried (MgSO4)
filtrationfiltered
customvolatiles removed in vacuo
customto afford a colourless oil

Sources & evidence

ORD record: ord-fc17ea7fad814190b4a3c5466c4e9cd0
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221756B2

Reaction notes

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