Acetyl chloride → HCID 136613157, compound

HRID 570911Notes

Reaction equation

HRID 570911 reaction equation
C(OC([NH:8][N:9]1[CH2:14][C:13](/[CH:15]=[N:16]/[O:17][CH3:18])=[N:12][N:11](C(OC(C)(C)C)=O)[C:10]1=[O:26])=O)(C)(C)C.C(Cl)(=O)C.C([O-])(O)=O.[Na+]>CO>[NH2:8][N:9]1[CH2:14][C:13](/[CH:15]=[N:16]/[O:17][CH3:18])=[N:12][NH:11][C:10]1=[O:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 89601899HCID 89601899, compound

Product 1

HCID 136613157HCID 136613157, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(tert-butoxycarbonylamino)-6-[(E)-methoxyiminomethyl]-3-oxo-5H-1,2,4-triazine-2-carboxylate (12.4 g, 30.0 mmol) in MeOH (120 mL) at 0° C. was slowly added acetyl chloride (10.7 mL, 150 mmol). After completion of the addition, the reaction mixture was stirred at this temperature for another 30 min before it was allowed to warm to room temperature. After additional 20 h stirring at room temperature, the reaction mixture was carefully neutralized with sat. NaHCO3. The volatiles were removed in vacuo and the residual was repeatedly diluted with acetonitrile and evaporated. The remaining material 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 0.42 min. [M+H]+ 172.

Workup

  1. customat 0° C.
  2. additionAfter completion of the addition
  3. stirringAfter additional 20 h stirring at room temperature
  4. customThe volatiles were removed in vacuo
  5. additionthe residual was repeatedly diluted with acetonitrile
  6. customevaporated
  7. stirringThe remaining material were stirred for 10 min with hot acetonitrile
  8. filtrationfiltered

Sources & evidence

ORD record
ord-403e6e22dbc04cedbdea25c3bcf38e94
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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