Sodium Methoxide → HCID 11579769, compound

HRID 1404322Notes

Reaction equation

HRID 1404322 reaction equation
C([O:9][CH:10]1[C:14]([F:16])([CH3:15])[CH:13]([N:17]2[CH:22]=[CH:21][C:20]([NH:23]C(=O)C3C=CC=CC=3)=[N:19][C:18]2=[O:32])[O:12][CH:11]1[CH2:33][O:34]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[NH2:23][C:20]1[CH:21]=[CH:22][N:17]([CH:13]2[C:14]([F:16])([CH3:15])[CH:10]([OH:9])[CH:11]([CH2:33][OH:34])[O:12]2)[C:18](=[O:32])[N:19]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58701526HCID 58701526, compound

Product 1

HCID 11579769HCID 11579769, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A slurry of 14 (14.7 kg) in MeOH (92.6 kg) is treated with catalytic amounts of methanolic sodium methoxide (0.275 kg). The reaction mixture is heated to ca. 50° C. and aged (ca. 1 h) until the hydrolysis is complete. The reaction mixture is quenched by addition of isobutyric acid (0.115 kg). The resulting solution is concentrated under moderate vacuum and then residual solvents are replaced with IPA (80 kg). The batch is distilled to a volume of ca. 50 L. The resulting slurry is heated to ca. 80° C. and then cooled slowly to ca. 5° C. and aged (ca. 2 h). The precipitated product is isolated by filtration, washed with IPA (16.8 kg) and dried in an oven at 70° C. in vacuo to afford 6.26 kg (88.9%) of 18 which assayed at 99.43% pure

Workup

  1. customaged (ca. 1 h)
  2. customThe reaction mixture is quenched by addition of isobutyric acid (0.115 kg)
  3. concentrationThe resulting solution is concentrated under moderate vacuum
  4. distillationThe batch is distilled to a volume of ca. 50 L
  5. temperatureThe resulting slurry is heated to ca. 80° C.
  6. temperaturecooled slowly to ca. 5° C.
  7. customaged (ca. 2 h)
  8. customThe precipitated product is isolated by filtration
  9. washwashed with IPA (16.8 kg)
  10. customdried in an oven at 70° C. in vacuo

Sources & evidence

ORD record
ord-a301604a60a343d8ac29c423f0dab3cc
Source dataset
uspto-grants-2014_12
Patent number
US08912321B2

Reaction notes

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