Water → HCID 10232658, compound

HRID 895929

Reaction equation

HRID 895929 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]([NH:11][C@H:12]([C:33]([OH:35])=[O:34])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:32])[N:22]([CH3:31])[C:23]([CH3:30])=[CH:24][C:25]=2[C:26]([F:29])([F:28])[F:27])=[CH:16][CH:15]=1)=[O:10].C(=O)(O)[O-].[Na+].[C:41]([O:44][CH:45](Cl)[CH3:46])(=[O:43])[CH3:42].O>CN(C=O)C>[C:41]([O:44][CH:45]([O:34][C:33](=[O:35])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:32])[N:22]([CH3:31])[C:23]([CH3:30])=[CH:24][C:25]=2[C:26]([F:28])([F:29])[F:27])=[CH:18][CH:19]=1)[NH:11][C:9]([C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:10])[CH3:46])(=[O:43])[CH3:42]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5218651-Chloroethyl acetateHCID 9806910RO-0505376

Product 1

HCID 10232658HCID 10232658, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine (145 mg, 0.275 mmol) and sodium bicarbonate (185 mg, 2.2 mmol) in DMF (2 mL) was added 1-chloroethyl acetate (270 mg, 2.2 mmol) at room temperature. The mixture was stirred for 48 h at room temperature. Then, the reaction mixture was poured into water (30 mL) and was extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with brine solution (60 mL) and were dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration gave the crude product, which was purified by silica gel chromatography using a Biotage (40 s) column to afford 110 mg (65% yield) of N-[(2,6-dichlorophenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine 1-(acetoxy)ethyl ester as an amorphous white solid. ES-HRMS m/e calcd for C28H25Cl2F3N2O6 (M+Na) 635.0931. found 635.0932.

Workup

  1. extractionwas extracted with ethyl acetate (3×20 mL)
  2. washThe combined organic extracts were washed with brine solution (60 mL)
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. filtrationFiltration of the drying agent and concentration
  5. customgave the crude product, which
  6. customwas purified by silica gel chromatography
  7. customa Biotage (40 s) column

Sources & evidence

ORD record
ord-4467d180a4034336b0e5a79256d06785
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Linked notes

Loading…