Ammonium formate → HCID 54385960, compound

HRID 965140Notes

Reaction equation

HRID 965140 reaction equation
[CH2:1]([O:8][C:9](=[O:43])[CH:10]([C:39]([O:41]C)=[O:40])[C@H:11]([C:16](=[O:38])[NH:17][C@H:18]1[CH2:35][C:34]2=[CH:36][N:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=32)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[O:37])[CH2:12][CH:13]([CH3:15])[CH3:14])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][O:8][C:9]([CH:10]([C@H:11]([C:16](=[O:38])[NH:17][C@H:18]1[CH2:35][C:34]2=[CH:36][N:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=32)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[O:37])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:39]([OH:41])=[O:40])=[O:43]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67693951(3R,10S)-2-methoxycarbonyl-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid benzyl ester

Product 1

HCID 54385960HCID 54385960, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Alternatively, (3R,10S)-2-methoxycarbonyl-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid benzyl ester was taken up in ethanol (35 mL, some heating was required) and ammonium formate 1642 mg, 3 eq) was added followed by 10% Pd on activated charcoal (100 mg). After stirring under argon at room temperature for 3 hrs. the reaction was complete. The mixture was suction-filtered through a 1 cm bed of celite, then it was concentrated, MeOH was added and it was filtered through a plug of cotton. After concentrating, CH2Cl2 was added to the residue and it was stirred vigorously and then filtered. The filtrate was concentrated and recrystallized from ethyl acetate/pet. ether to give (3R,10S)-2-methoxycarbonyl-5-methyl-3-(9-oxo-1,8-diazatricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid as a white solid (yield: 140 mg), MS: 500.3 (M+H)+.

Workup

  1. additionwas added
  2. filtrationThe mixture was suction-filtered through a 1 cm bed of celite
  3. concentrationit was concentrated
  4. additionMeOH was added
  5. filtrationit was filtered through a plug of cotton
  6. concentrationAfter concentrating
  7. additionCH2Cl2 was added to the residue and it
  8. stirringwas stirred vigorously
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customrecrystallized from ethyl acetate/pet. ether

Sources & evidence

ORD record
ord-37bffd049fa84b09b2150d97ca0d1fe9
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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