Pyridine → 3-[3-(1-Benzyloxycarbonylamino-3-methyl-butyl)-isoxazol-5-yl]-acrylic acid ethyl ester

HRID 381521Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH:11]([C:16]1[CH:20]=[C:19]([CH:21]=O)[O:18][N:17]=1)[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:30]([O:36][CH2:37][CH3:38])(=[O:35])[CH2:31]C(O)=O>O>[CH2:37]([O:36][C:30](=[O:35])[CH:31]=[CH:21][C:19]1[O:18][N:17]=[C:16]([CH:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:23])[CH2:12][CH:13]([CH3:14])[CH3:15])[CH:20]=1)[CH3:38]

Participants

Conditions

Temperature: 55 °C

Procedure

A stirred mixture of [1-(5-formyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid benzyl ester (407 mg, 1.3 mmol), pyridine (10 ml) and ethyl hydrogen malonate (255 mg, 1.9 mmol) was warmed to 55° C. After 2 days the mixture was cooled to room temperature, poured into water and extracted into EtOAc (3×). The combined organics were washed with 1N HCl, water, and brine; dried over NaSO4, filtered and concentrated under reduced pressure to give 480 mg of a yellow oil. Purification by Flash 40(small) chromatography eluting with 1:3 EtOAc/hexane gave 220 mg of the title compound as a light yellow oil. MS [M+1]+ 387.

Workup

temperatureAfter 2 days the mixture was cooled to room temperature
extractionextracted into EtOAc (3×)
washThe combined organics were washed with 1N HCl, water, and brine
dry with materialdried over NaSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-43210986965f48c0a91bf393a18d75fe
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306887B1

Reaction notes

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