Acetic Acid → Acetic Acid [5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]-oxadiazol-3-yl)phenyl]tert-butylcarbamoylmethyl Ester

HRID 2075956Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([N+:29]#[C-:30])([CH3:28])([CH3:27])[CH3:26].[C:31](O)(=[O:33])[CH3:32].C(#N)C.[OH2:38]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:13]([CH:14]([O:15][C:31](=[O:33])[CH3:32])[C:30](=[O:38])[NH:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzaldehyde (Reference example 15-1) (453 mg), tert-butylisocyanide (465 mg), acetic acid (0.32 mL) and acetonitrile (8 mL) was stirred at 70° C. for 13 hours. After cooling to room temperature, ethyl acetate and water were added to the mixture. The separated organic layer was washed with water, an aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution) to give the title compound (604 mg).

Workup

temperatureAfter cooling to room temperature
washThe separated organic layer was washed with water
dry with materialan aqueous solution of sodium bicarbonate, and brine successively, dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record: ord-725ea753136447e5be442f51724feb1e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923462B2

Reaction notes

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