Triethylamine → HCID 89534508, compound

HRID 1528206Notes

Reaction equation

HRID 1528206 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=O.Cl.[NH:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([O:23][CH3:24])=[O:22].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>S(Cl)(Cl)=O.ClCCl>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([O:23][CH3:24])=[O:22])=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 3026292,6-Difluoro-3-nitrobenzoic acidHCID 516892Sodium BicarbonateHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 89534508HCID 89534508, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.82 g (8.94 mmol) of 2,6-difluoro-3-nitrobenzoic acid in 36 ml of thionyl chloride was refluxed for three and a half hours. The reaction medium was concentrated and was co-evaporated twice with toluene. The residue obtained was dissolved in 50 ml of dichloromethane under nitrogen. 1.48 g (8.94 mmol) of methyl (S)-pyrrolidine-2-carboxylate hydrochloride were added and the reaction medium was cooled to 0° C. 2.75 ml (19.67 mmol, 2.2 eq) of triethylamine were then added dropwise. After 22 hours, a saturated aqueous sodium hydrogen carbonate solution was added. The organic phase was again washed with a saturated aqueous sodium hydrogen carbonate solution and then twice more with a 1 M aqueous hydrochloric acid solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. 2.52 g were obtained. Yield=83%.

Workup

  1. concentrationThe reaction medium was concentrated
  2. customThe residue obtained
  3. washThe organic phase was again washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custom2.52 g were obtained

Sources & evidence

ORD record
ord-d8f7161920b5409d84060584e97514b6
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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