Ammonium formate → HCID 10135305, compound

HRID 2182952Notes

Reaction equation

HRID 2182952 reaction equation
C([O:8][NH:9][C:10](=[O:35])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:34])=[C:25]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[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.[OH-].[Pd+2].[OH-]>[CH:16]1([CH2:15][CH2:14][CH2:13][C@@H:12]([C:22]2[O:23][C:24]([CH3:34])=[C:25]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])[N:26]=2)[CH2:11][C:10]([NH:9][OH:8])=[O:35])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59909765HCID 59909765, compound

Product 1

HCID 10135305HCID 10135305, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
43 °C

Procedure

A solution ({[2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-5-methyl-1,3-oxazol-4-yl]carbonyl}amino)acetic acid (Preparation 100) (60 mg, 0.12 mmol) in ethanol (3 ml) was treated with ammonium formate (78 mg, 1.23 mmol) and palladium hydroxide (20 mg) and heated at 43° C., under a nitrogen atmosphere for 4 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 99:1:0.1 (dichloromethane:methanol:acetic acid) gradually changing to 90:10:1 (dichloromethane:methanol:acetic acid) to afford the title compound as a white solid (17 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 99:1:0.1 (dichloromethane:methanol:acetic acid)

Sources & evidence

ORD record
ord-659f709e5acf454c86b15d4983af8268
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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