Ammonium formate → HCID 9923900, compound

HRID 2182936Notes

Reaction equation

HRID 2182936 reaction equation
C([O:8][NH:9][C:10](=[O:31])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:30])=[C:25]([C:27]([NH2:29])=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH3:9].[CH:16]1([CH2:15][CH2:14][CH2:13][C@@H:12]([C:22]2[O:23][C:24]([CH3:30])=[C:25]([C:27]([NH2:29])=[O:28])[N:26]=2)[CH2:11][C:10]([NH:9][OH:8])=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 59909844HCID 59909844, compound

Product 2

HCID 222AmmoniaHCID 9923900HCID 9923900, compoundYield 107.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-5-methyl-1,3-oxazole-4-carboxamide (Preparation 74) (133 mg, 0.31 mmol) in ethanol (6 ml) was treated with 5% palladium on barium sulphate (80 mg) and ammonium formate (196 mg, 3.10 mmol) and the mixture was heated at 45° C. for 2.5 hours. The solution was filtered through Arbocel® and the solvent removed from the filtrate under reduced pressure. The residue was azeotroped from dichloromethane (×3) then purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (98:2:0.2 to 90:10:1) to afford the title compound as a white solid (56 mg).

Workup

  1. filtrationThe solution was filtered through Arbocel®
  2. customthe solvent removed from the filtrate under reduced pressure
  3. customThe residue was azeotroped from dichloromethane (×3)
  4. customthen purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-d41369d9419d40918f670c1e534f495f
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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