Triethyl orthoacetate → HCID 68710756, compound

HRID 2067944Notes

Reaction equation

HRID 2067944 reaction equation
O[N:2]=[C:3]([C:9](=O)[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[NH2:17].[C:25]1(C)C=CC(S([O-])(=O)=O)=C[CH:26]=1.[NH+]1C=CC=CC=1.C(OCC)(OCC)(OCC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.[Pd]>[CH2:7]([O:6][C:4]([C:3]1[N:2]=[C:25]([CH3:26])[N:17]([C:16]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:14]([C:13]([F:23])([F:24])[F:12])[CH:15]=2)[C:9]=1[CH3:10])=[O:5])[CH3:8]

Participants

8

Reactant 5

HCID 66221Triethyl orthoacetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 521998p-Toluenesulfonic acid monohydrateHCID 6007055-Amino-2-methoxybenzotrifluorideHCID 178472877HCID 178472877, compound

Product 1

HCID 68710756HCID 68710756, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Ethyl 2-Hydroxyimino-3-oxobutanoate (1.67 g, 10.5 mmol) (Example C), 3-trifluoromethyl-4-methoxyaniline (2.0 g, 10.5 mmol) and pyridinium p-toluenesulfonate (0.13 g, 0.52 mmol) were stirred at 75° C. in toluene (15 ml) for 4 hrs. The reaction mixture was evaporated under vacuum at 40° C. The residue was dissolved in triethyl orthoacetate (14.3 ml, 78 mmol) and p-toluenesulfonic acid monohydrate (0.1 g, 0.52 mmol), and palladium on charcoal (0.6 g) were added. The reaction mixture was stirred for 4 hrs under hydrogen atmosphere. The dark suspension was filtered and evaporated to dryness. The crude product was recrystallized at 0° C. from TBME and n-heptane. The desired product was obtained as a light brown solid (1.28 g, 36%), MS: m/e=343.1 (M+H+).

Workup

  1. customThe reaction mixture was evaporated under vacuum at 40° C
  2. filtrationThe dark suspension was filtered
  3. customevaporated to dryness
  4. customThe crude product was recrystallized at 0° C. from TBME and n-heptane

Sources & evidence

ORD record
ord-dba325c21e284d47a2ff81b7390743db
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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