Ammonium formate → HCID 10179648, compound

HRID 2182951Notes

Reaction equation

HRID 2182951 reaction equation
C([O:8][NH:9][C:10](=[O:36])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:35])=[C:25]([C:27]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[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]>[CH:16]1([CH2:15][CH2:14][CH2:13][C@@H:12]([C:22]2[O:23][C:24]([CH3:35])=[C:25]([C:27]([NH:29][CH2:30][CH2:31][N:32]([CH3:33])[CH3:34])=[O:28])[N:26]=2)[CH2:11][C:10]([NH:9][OH:8])=[O:36])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59909856HCID 59909856, compound

Product 1

HCID 10179648HCID 10179648, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
43 °C

Procedure

A solution 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-N-[2-(dimethylamino)ethyl]-5-methyl-1,3-oxazole-4-carboxamide (Preparation 98) (193 mg, 0.39 mmol) in ethanol (10 ml) was treated with ammonium formate (244 mg, 3.90 mmol) and 5% palladium on barium sulphate (100 mg) and heated at 43° C., under a nitrogen atmosphere for 2 hours. The reaction mixture was filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of 98:2:0.2 (dichloromethane:methanol:ammonia) gradually changing to 90:10:1 (dichloromethane:methanol:ammonia) to afford the title compound as a white solid (80 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of 98:2:0.2 (dichloromethane:methanol:ammonia)

Sources & evidence

ORD record
ord-cebbcd0be8034fecb1dbe9911baf5ca5
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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