Acetyl chloride → HCID 89601929, compound

HRID 570919Notes

Reaction equation

HRID 570919 reaction equation
C(OC([NH:8][N:9]1[CH2:14][C:13]([C:15]2[CH2:19][C:18]([CH3:21])([CH3:20])[O:17][N:16]=2)=[N:12][N:11](C(OC(C)(C)C)=O)[C:10]1=[O:29])=O)(C)(C)C.C(Cl)(=O)C.C[O-].[Na+]>CCO.CO>[NH2:8][N:9]1[CH2:14][C:13]([C:15]2[CH2:19][C:18]([CH3:20])([CH3:21])[O:17][N:16]=2)=[N:12][NH:11][C:10]1=[O:29]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 10942334Sodium MethoxideHCID 89601751HCID 89601751, compound

Product 1

HCID 89601929HCID 89601929, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(tert-butoxycarbonylamino)-6-(5,5-dimethyl-4H-isoxazol-3-yl)-3-oxo-5H-1,2,4-triazine-2-carboxylate (2.50 g, 5.51 mmol) in EtOH (30 mL) at 0° C. was slowly added acetyl chloride (2.16 mL, 27.6 mmol). After completion of the addition, the reaction mixture was allowed to warm to room temperature and stirring was continued for an additional 20 h. The reaction mixture was cooled to 0° C. and carefully treated with NaOMe in MeOH until pH 7 was reached. The volatiles were removed in vacuo and the residual was repeatedly diluted with acetonitrile and evaporated. The remaining solids were stirred for 10 min with hot acetonitrile and filtered. Concentration of the filtrate furnished the desired product as an off-white solid. LCMS (Method K) RT 0.47 min. [M+H]+ 212.

Workup

  1. customat 0° C.
  2. additionAfter completion of the addition
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customThe volatiles were removed in vacuo
  5. additionthe residual was repeatedly diluted with acetonitrile
  6. customevaporated
  7. stirringThe remaining solids were stirred for 10 min with hot acetonitrile
  8. filtrationfiltered

Sources & evidence

ORD record
ord-1c0494de84244c82a053a7d6dfd66e91
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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