Sodium Carbonate → HCID 90024636, compound

HRID 523967Notes

Reaction equation

HRID 523967 reaction equation
C(O[CH2:5][C:6]1[C:15]2[C:10](=[C:11]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:12]=[CH:13][CH:14]=2)[C:9]([OH:23])=[C:8]([C:24]([O:26][CH3:27])=[O:25])[N:7]=1)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C(OCC)(=O)C>[OH:23][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6]([CH3:5])=[N:7][C:8]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 90025454HCID 90025454, compound

Product 1

HCID 90024636HCID 90024636, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A glass lined Parr pressure reactor vessel equipped with a 4-blade impeller can be charged with 1c, Pd/C (about 0.4 to 0.5 molar equivalents), anhydrous Na2CO3 (about 0.5 molar equivalents), and ethyl acetate. The flask can then be vacuum-purged with nitrogen (3×) and vacuum-purged with hydrogen (3×). The flask can then be pressurized with hydrogen to set point 60 psi and stirred at 60° C. for 6-8 hrs until completion of reaction (1c <0.5%). The flask can then be cooled to 20-25° C., the pressure released to ambient, the head space purged with nitrogen three times and filtered through glass microfiber filter paper. The filtrate can be concentrated and precipitated from cold methanol and dried under vacuum at 50±5° C.

Workup

  1. customequipped with a 4-blade impeller
  2. customThe flask can then be vacuum-purged with nitrogen (3×)
  3. customvacuum-purged with hydrogen (3×)
  4. temperatureThe flask can then be cooled to 20-25° C.
  5. customthe head space purged with nitrogen three times
  6. filtrationfiltered through glass microfiber
  7. filtrationfilter paper
  8. concentrationThe filtrate can be concentrated
  9. customprecipitated from cold methanol
  10. customdried under vacuum at 50±5° C.

Sources & evidence

ORD record
ord-56242c4239dd4e419f4292a7d92e4112
Source dataset
uspto-grants-2016_05
Patent number
US09340511B2

Reaction notes

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