Methanol → HCID 19858589, compound

HRID 2072604Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:18]([O-:20])=[O:19])=[C:9]([NH:11][CH:12](C)[CH2:13][C:14](O)=O)[CH:10]=1.C(N(CC)CC)C.Cl[C:37]([O:39][CH3:40])=[O:38].CO>C1(C)C=CC=CC=1.O.CCOCC>[CH3:40][O:39][C:37](=[O:38])[CH2:14][CH2:13][CH2:12][NH:11][C:9]1[CH:10]=[C:5]([O:4][C:3]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:26])[F:27])=[CH:24][C:2]=2[Cl:1])[CH:6]=[CH:7][C:8]=1[N+:18]([O-:20])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3-[5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrophenylamino]butyric acid (2.50 gm, 5.97 mmol) in 50 ml toluene cooled to 0° C. was added triethylamine (0.83 ml, 5.97 mmol). Methyl chloroformate (0.51 ml, 6.57 mmol) was added. After 1 hour the reaction was warmed to room temperature, an excess of methanol was added and the mixture was allowed to stir overnight. The reaction mixture was diluted with water, ether extracted, shaken with brine and dried (MgSO4) filtered and concentrated under vacuum. The resulting viscous oil was purified by column chromatography, silica gel, 40% ether/hexane to afford 2 gm of the desired product.

Workup

temperatureAfter 1 hour the reaction was warmed to room temperature
extractionextracted
stirringshaken with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under vacuum
customThe resulting viscous oil was purified by column chromatography, silica gel, 40% ether/hexane

Sources & evidence

ORD record: ord-a8701ba6287a48a6b056b440a6ed5066
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04913729

Reaction notes

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