Methyl chloroglyoxylate → HCID 68889341, compound

HRID 1821000Notes

Reaction equation

HRID 1821000 reaction equation
[F:1][C:2]([F:36])([CH:8](O)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=3)[CH2:18][O:17][N:16]=2)=[C:11]([CH3:34])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].ClC(=O)C(OC)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl.CCOC(C)=O>[F:36][C:2]([F:1])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:28])[CH3:29])=[C:22]([C:30]([F:31])([F:32])[F:33])[CH:21]=3)[CH2:18][O:17][N:16]=2)=[C:11]([CH3:34])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 2

HCID 79846Methyl chloroglyoxylateHCID 68888548HCID 68888548, compound

Product 1

HCID 68889341HCID 68889341, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 29 mg (0.06 mmol) of ethyl 2,2-difluoro-3-hydroxy-3-(4-(4-(4-(isopropoxy)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate (from EXAMPLE 75, Step D) and 21 mg (0.17 mmol) of 4-dimethylaminopyridine in 5.0 mL of CH2Cl2 at ° C. was added 10 μL (0.11 mmol) of methyl chlorooxoacetate. After stirring at 0° C. for 10 min and rt for 20 min, the reaction mixture was diluted with 20 mL of EtOAc and washed with diluted HCl (10 mL), saturated NaHCO3 (10 mL), and brine (10 mL). The organic layer was dried over MgSO4 and concentrated to give the crude ester product.

Workup

  1. washwashed with diluted HCl (10 mL), saturated NaHCO3 (10 mL), and brine (10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-519d60636a574065bd08e87e4eeb823b
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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