Hydrochloric Acid → HCID 13127265, compound

HRID 1758255Notes

Reaction equation

HRID 1758255 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].Cl.O>C(O)C>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]2[N:12]=[C:11]([CH:22]([C:23]([F:25])([F:26])[F:24])[OH:27])[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 13127291HCID 13127291, compound

Product 1

HCID 13127265HCID 13127265, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3.8 g (10 mmoles) of the compound of Example 9 in 50 ml ethanol chilled to 0°-5°, was added 1.0 g (25 mmoles) sodium borohydride all at once. After 0.5 hour at that temperature, the cooling was discontinued, and the reaction was allowed to proceed at room temperature for 1 hour. The reaction mixture was then chilled to 0°-10° C., and 40 ml of 2 N HCl was cautiously added, followed by another 40 ml of water. Most of the ethanol was removed under vacuo. The crystalline product was collected by filtration, washed with water, and air dried. Recrystallization from acetonitrile yielded 3.9 of the title compound, m.p. 242°-245°. The infrared and NMR spectra were consistent with the assigned structure.

Workup

  1. waitto proceed at room temperature for 1 hour
  2. temperatureThe reaction mixture was then chilled to 0°-10° C.
  3. customMost of the ethanol was removed under vacuo
  4. filtrationThe crystalline product was collected by filtration
  5. washwashed with water, and air
  6. customdried
  7. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-93339b6e7e054515b752d6c77550ffe3
Source dataset
uspto-grants-1983_02
Patent number
US04372964

Reaction notes

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