Ammonium formate → HCID 10179648, compound

HRID 1279799Notes

Reaction equation

HRID 1279799 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-65056437ad6d44a0a6c5af90f0f43167
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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