Triethylamine → HCID 14720611, compound

HRID 477868

Reaction equation

HRID 477868 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.Cl.[CH3:17][O:18][C:19](=[O:28])[C@H:20]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[NH2:21].C(N(CC)CC)C>CN(C)C=O.CN(C)C1C=CN=CC=1.C(Cl)Cl.C1C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:21][C@H:20]([C:19]([O:18][CH3:17])=[O:28])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:6]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27745162-Fluoro-4-iodobenzoic acidHCID 12917568Dimethyl L-glutamate hydrochloride

Product 1

HCID 14720611HCID 14720611, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 20 mL of benzene are added 2.0 g (0.00752 mol) of 2-fluoro4-iodobenzoic acid, followed by 2.3 mL (320 mmol) of thionyl chloride and several drops of dimethylformamide. The mixture is heated at reflux of 3.5 hours. The solvent is then removed in vacuo and the residue pumped dry. The resulting acid chloride is redissolved in 10 ml of methylene chloride, and added dropwise to cooled mixture of 1.67 g (7.89 mmol) of L-glutamic acid dimethyl ester hydrochloride, 5 mg of 4-dimethylaminopyridine, and 2.2 mL (15.8 mmol) of triethylamine in 30 mL of methylene chloride. After the addition, the reaction stirred at room temperature for 18 hours. The reaction mixture is then diluted with additional methylene chloride, washed with 1N hydrochloric acid, water and 5% sodium bicarbonate and dried over sodium sulfate. The solvent is removed in vacuo to give 2.34 g (74%) of dimethyl N-(2-fluoro-4-iodobenzoyl)-L-glutamate as a white solid m.p. 94°-96° C.; IR (KBr, cm-1)=1159, 1177, 1194, 1208, 1229, 1398, 1437, 1477, 1537, 1601, 1642, 1728, 1739, 1756, 3326.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux of 3.5 hours
  3. customThe solvent is then removed in vacuo
  4. customthe residue pumped dry
  5. dissolutionThe resulting acid chloride is redissolved in 10 ml of methylene chloride
  6. additionadded dropwise
  7. temperatureto cooled
  8. additionAfter the addition
  9. washwashed with 1N hydrochloric acid, water and 5% sodium bicarbonate
  10. dry with materialdried over sodium sulfate
  11. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-42430265d92c41e7a5c2bd056593e131
Source dataset
uspto-grants-1989_12
Patent number
US04889859

Linked notes

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