p-Toluenesulfonic acid → 3-(3-(1,2,4-Oxadiazol-3-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

HRID 909911Notes

Reaction equation

[CH:1]1([N:7]([CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[C:8](=[O:24])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[NH:23])[NH:21][OH:22])[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:31](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[O:22]1[CH:31]=[N:23][C:20]([C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9][C:8]([N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])=[O:24])=[N:21]1

Participants

Conditions

Temperature: 100 °C

Procedure

To N-cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(N-hydroxycarbamimidoyl)phenethoxy)propanamide [Example 11, Step i)] (530 mg) in a 10 mL microwave vial was added trimethyl orthoformate (1 mL), sealed and heated at 100° C. for 20 min. The vial was then heated to 120° C. for 3 h before the addition of p-toluenesulfonic acid (3 mg) and then heated to 120° C. for a further 60 min. Ethanol was added (30 mL) and the solvent was evaporated to afford the sub-titled compound (500 mg). MS [M+H-MeOH]+=400 (MultiMode+)

Workup

customsealed
temperatureheated to 120° C. for a further 60 min
customthe solvent was evaporated

Sources & evidence

ORD record: ord-bedab30dfc624b43a9f22ab61ad7eac4
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017602B2

Reaction notes

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