Sodium Chloride → HCID 67130093, compound

HRID 2279257Notes

Reaction equation

HRID 2279257 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@@H:13]([C:14]([OH:16])=[O:15])[CH2:12][N:11]([CH3:17])[C:10]2=[O:18])=[CH:5][C:4]=1[C:19]([F:22])([F:21])[F:20])#[N:2].[N+](=[CH2:25])=[N-].[Na+].[Cl-]>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@@H:13]([C:14]([O:16][CH3:25])=[O:15])[CH2:12][N:11]([CH3:17])[C:10]2=[O:18])=[CH:5][C:4]=1[C:19]([F:21])([F:22])[F:20])#[N:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 9550DiazomethaneHCID 67130092HCID 67130092, compound

Product 1

HCID 67130093HCID 67130093, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-(4-cyano-3-(trifluoromethyl)phenyl)-1-methyl-2-oxoimidazolidine-4-carboxylic acid (25e) (0.280 g, 0.894 mmol) in THF (10 mL), cooled to 0° C., Diazomethane [prepared from N-Nitrosomethyl urea (0.276 g, 2.68 mmol) and 40% KOH solution (15 mL) in ether (10 mL)] was added under nitrogen atmosphere. The resulting reaction mixture was warmed up to room temperature and stirred for 1 h. After completion (by TLC), the reaction mixture was poured into saturated NaCl solution and extracted with EtOAc (2×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to provide the crude residue which was purified by column chromatography to afford the methyl ester 25f (0.210 g, 72%) as a colorless syrup.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto provide the crude residue which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-0dbca7db935c46c2a981aa44f76924bc
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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