Triethylamine → HCID 89533690, compound

HRID 1050973Notes

Reaction equation

[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:15][O:16][C:17](=[O:23])[C@@H:18]1[CH2:22][CH2:21][CH2:20][NH:19]1.C(N(CC)CC)C>S(Cl)(Cl)=O>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:19]1[CH2:20][CH2:21][CH2:22][C@H:18]1[C:17]([O:16][CH3:15])=[O:23])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 18.51 g (0.10 mol; 1.0 eq) of 2-fluoro-3-nitrobenzoic acid and 100 ml of thionyl chloride was refluxed for 3 hours. The excess thionyl chloride was then concentrated and the residue was co-evaporated twice with toluene. The resulting acid chloride was taken up in 250 ml of dichloromethane. To this mixture, cooled to 0° C., were added 16.56 g (0.10 mol; 1.0 eq) of L-proline methyl ester hydrochloride and then 30.50 ml (0.22 mol; 2.2 eq) of triethylamine. After 30 minutes at 0° C. and one hour at ambient temperature, the reaction medium was diluted and washed with 250 ml of a 1 M aqueous hydrochloric acid solution and then with 250 ml of a saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. 25.64 g of methyl (S)-1-(2-fluoro-3-nitrobenzoyl)pyrrolidine-2-carboxylate were obtained. Yield=87%.

Workup

temperaturewas refluxed for 3 hours
concentrationThe excess thionyl chloride was then concentrated
additionone hour at ambient temperature, the reaction medium was diluted
washwashed with 250 ml of a 1 M aqueous hydrochloric acid solution
dry with materialThe organic phase was dried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-c3dbdd7ed44d4601b0c9978a3da28e5d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388149B2

Reaction notes

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