Ammonium formate → HCID 178498179, compound

HRID 1053829Notes

Reaction equation

HRID 1053829 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C@@H:14]2[CH2:18][N:17]([C:19]([C@H:21]3[CH2:26][CH2:25][C@@H:24]([CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][CH2:22]3)=[O:20])[C@H:16]([C:36]([NH:38][C:39]3[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=3)=[O:37])[CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:35][C:32]([O:31][C:29]([NH:28][CH2:27][C@@H:24]1[CH2:25][CH2:26][C@H:21]([C:19]([N:17]2[CH2:18][C@@H:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH2:15][C@H:16]2[C:36]([NH:38][C:39]2[CH:40]=[CH:41][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:47][CH:48]=2)=[O:37])=[O:20])[CH2:22][CH2:23]1)=[O:30])([CH3:33])[CH3:34]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178498180HCID 178498180, compound

Product 1

HCID 178498179HCID 178498179, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask under nitrogen was added the compound prepared in Example 49 (0.90 g), ammonium formate (2.57 g) and palladium on carbon (1.61 g). Methanol was added (45 mL) under nitrogen and the reaction heated at reflux for 2.5 h. The reaction mixture was cooled and filtered through Celite®, washing the filter cake with methanol. The solvent was removed in vacuo, diluted with water and extracted with ethyl acetate. The combined ethyl acetate fractions were washed with brine, dried and concentrated to give the title compound (0.57 g) as a colourless solid.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 2.5 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through Celite®
  5. washwashing the filter cake with methanol
  6. customThe solvent was removed in vacuo
  7. additiondiluted with water
  8. extractionextracted with ethyl acetate
  9. washThe combined ethyl acetate fractions were washed with brine
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ad7801478e824a7a8147bea9271b3aa6
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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