Methyl N-(triethylammoniosulfonyl)carbamate → HCID 71598840, compound

HRID 1507728Notes

Reaction equation

[C:1]([NH:4][NH:5][C:6]([C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:10]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]=1[O:34][CH2:35]C1C=CC=CC=1)=[O:7])(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)([CH2:47][CH3:48])CC>C1COCC1>[CH2:27]([O:26][C:10]1[C:9]([O:34][CH2:35][C:48]2[CH:47]=[CH:10][CH:9]=[CH:8][CH:6]=2)=[C:8]([C:6]2[O:7][C:1]([CH3:2])=[N:4][N:5]=2)[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:11]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-5-(2-acetylhydrazinecarbonyl)-1H-pyrrole-2-carboxylate (31) (155 mg, 0.56 mmol) and Burgess reagent (132 mg, 0.56 mmol) were dissolved in THF (2 mL). The mixture was heated in a microwave at 100° C. for 30 min and the volatiles removed in vacuo. The crude product was purified by silica gel chromatography (12 g, 0-30% EtOAc in isohexane) to afford ethyl 3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrole-2-carboxylate (UL1-087) (115 mg, 77%) as a colourless oil: m/z 540 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.46 (m, 2H), 7.43-7.31 (m, 8H), 7.18-7.12 (m, 2H), 6.93-6.87 (m, 2H), 5.17 (s, 2H), 5.07 (s, 2H), 4.02 (q, J=7.1 Hz, 2H), 3.78 (s, 3H), 2.35 (s, 3H), 1.01 (t, J=7.1 Hz, 3H).

Workup

customthe volatiles removed in vacuo
customThe crude product was purified by silica gel chromatography (12 g, 0-30% EtOAc in isohexane)

Sources & evidence

ORD record: ord-8bd5dad84af54466842e9f90f25982c8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221756B2

Reaction notes

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