Triethylamine → HCID 86598133, compound

HRID 490725Notes

Reaction equation

HRID 490725 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH:10]([CH3:14])[C:11]([OH:13])=O)=O)=[CH:5][CH:4]=1.[C:19](Cl)(=[O:23])C(Cl)=O.C(N(CC)CC)C.Cl.[CH3:33][NH:34][O:35][CH3:36]>CN(C=O)C>[CH3:36][O:35][N:34]([CH3:33])[C:19]([C:11]1[O:13][C:7]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:16][CH:15]=2)=[N:9][C:10]=1[CH3:14])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 21942791HCID 21942791, compound

Product 1

HCID 86598133HCID 86598133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-Trifluoromethyl-benzoylamino)-propionic acid (5.0 g, 19.14 mmol) is added oxalyl chloride (16.7 mL, 191.4 mmol) and 2 drops of DMF and the solution stirred overnight. The volatiles are removed in vacuo and toluene (20 mL) is added. The toluene is then removed in vacuo. To the resultant crude oil is dissolve in dichloromethane (100 mL), cooled to 0° C. and triethylamine (13.4 mL, 96 mmol) is added followed by N,O-dimethyl hydroxylamine hydrochloride (9.4 g, 96 mmol). After 1 hr the mixture is partitioned between 1M aqueous hydrochloric acid and ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo. The product is purified over silica eluting with 8:2 hexanes:ethyl acetate to afford 4-methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methoxy-methyl-amide as a white crystalline solid, 2.4 g, 40%. MS (M++1)315.

Workup

  1. customThe volatiles are removed in vacuo and toluene (20 mL)
  2. additionis added
  3. customThe toluene is then removed in vacuo
  4. dissolutionTo the resultant crude oil is dissolve in dichloromethane (100 mL)
  5. customAfter 1 hr the mixture is partitioned between 1M aqueous hydrochloric acid and ethyl acetate
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product is purified over silica eluting with 8:2 hexanes

Sources & evidence

ORD record
ord-6a6ecb2f437c4bcf9c2dcaf1380169c3
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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