Methylamine → HCID 178482460, compound

HRID 1510161Notes

Reaction equation

HRID 1510161 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:19])[C@@H:14]([CH3:28])[CH2:13]3)[C:11](=[NH:29])[NH:10][C:9]2=[O:30])[CH:5]=[CH:6][CH:7]=1.[CH3:31]N>C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[O:19])[C@@H:14]([CH3:28])[CH2:13]3)[C:11]([NH:29][CH3:31])=[N:10][C:9]2=[O:30])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 145723817921599-76-02×

Product 1

HCID 178482460HCID 178482460, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a flask containing benzyl (5R,7S)-4-amino-1-(3-fluorophenyl)-7-methyl-2-oxo-1,3,8-triazaspiro[4.5]dec-3-ene-8-carboxylate (343 mg, 0.86 mmol; Intermediate 11-6) was added methylamine (2.0 M THF, 4.3 mL, 8.6 mmol). The vessel was sealed and placed in a 70° C. oil bath and stirred overnight. The reaction was diluted with aqueous NaHCO3 and extracted with EtOAc (three times). The combined organic layers were washed with brine, isolated and subsequently dried over Na2SO4. Evaporation of solvent and further drying under vacuum gave crude product that was used in the next step.

Workup

  1. customThe vessel was sealed
  2. customplaced in a 70° C.
  3. extractionextracted with EtOAc (three times)
  4. washThe combined organic layers were washed with brine
  5. customisolated
  6. dry with materialsubsequently dried over Na2SO4
  7. customEvaporation of solvent
  8. customfurther drying under vacuum
  9. customgave crude product that

Sources & evidence

ORD record
ord-e0ba627e47ab4e79bd704ab5ee4bcf82
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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