4-Methoxybenzyl alcohol → ethyl 2-((N-(butyloxycarbonyl)-N-(p-methoxybenzyl)sulfamoyl)amino)acetate

HRID 16967

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:30]([O:34][C:35]([NH:37][S:38]([NH:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])(=[O:40])=[O:39])=[O:36])[CH2:31][CH2:32][CH3:33].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:30]([O:34][C:35]([N:37]([CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[S:38]([NH:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])(=[O:39])=[O:40])=[O:36])[CH2:31][CH2:32][CH3:33]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (4-methoxyphenyl)-methanol (1.4 g, 8.5 mmol) and triphenyl-phosphane (2.6 g, 8.5 mol) in dry THF was added a solution of ethyl 2-((N-(butyloxycarbonyl)sulfamoyl)amino)acetate from the previous step (2.4 g, 8.5 mol) and DIAD (2.0 g, 8.5 mmol) in dry THF dropwise at 0° C. under N2 atmosphere. The mixture was stirred at 0° C. for 2 h, warmed to RT and stirred overnight. After the solvent was removed in vacuo, the residue was purified by column chromatography to afford ethyl 2-((N-(butyloxycarbonyl)-N-(p-methoxybenzyl)sulfamoyl)amino)acetate (2.3 g, 69%) as a white solid. 1H-NMR (CDCl3): δ 7.32 (d, J=8.8 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 5.71 (m, 1H), 4.76 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 3.80 (s, 3H), 3.55 (d, J=5.2 Hz, 2H), 1.54 (s, 9H), 1.25 (t, J=7.2 Hz, 3H).

Workup

temperaturewarmed to RT
stirringstirred overnight
customAfter the solvent was removed in vacuo
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-32ec822684a44ab987aa9823d61c5656
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737283B2

Linked notes

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