Acetic Acid → HCID 19982205, compound

HRID 1460565Notes

Reaction equation

HRID 1460565 reaction equation
C([CH:3]1[CH2:8][CH2:7][CH2:6][O:5][CH2:4]1)=O.[NH2:9][C:10]1[C:19]([CH3:20])=[C:18]([F:21])[C:13]2[NH:14][C:15](=[O:17])[O:16][C:12]=2[CH:11]=1.[CH3:22]C(O)=O.C([BH3-])#N.[Na+]>CO>[F:21][C:18]1[C:13]2[NH:14][C:15](=[O:17])[O:16][C:12]=2[CH:11]=[C:10]([NH:9][CH2:22][CH:4]2[CH2:3][CH2:8][CH2:7][CH2:6][O:5]2)[C:19]=1[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 10129928Oxane-3-carbaldehydeHCID 15675937HCID 15675937, compound

Product 1

HCID 19982205HCID 19982205, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Formyltetrahydro-2H-pyran (12.9 g, 113 mmol) was added to a solution of 6-amino-4-fluoro-5-methyl-2-benzoxazolone (17.4 g, 96 mmol) in MeOH (600 ml). The mixture was stirred for 1 hour at room temperature. AcOH (1 ml) was added, followed by an addition of sodium cyanoborohydride (8.17 g, 130 mmol). Stirring was continued for 5 hours. The reaction mixture was concentrated in vacuo, and the residue was treated with water. This crude product was recrystallized from EtOH, to give the titled compound.

Workup

  1. stirringStirring
  2. waitwas continued for 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue was treated with water
  5. customThis crude product was recrystallized from EtOH

Sources & evidence

ORD record
ord-3dc2a6dd83e34fefa2d4e08c87b05d3c
Source dataset
uspto-grants-1991_12
Patent number
US05071863

Reaction notes

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