Ammonium formate → HCID 10270207, compound

HRID 1279787Notes

Reaction equation

HRID 1279787 reaction equation
C([O:8][NH:9][C:10](=[O:33])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:32])=[C:25]([C:27]([N:29]([CH3:31])[CH3:30])=[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]([CH3:32])=[C:25]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[N:26]=2)[CH2:11][C:10]([NH:9][OH:8])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 2

HCID 2723923Ammonium formate2×HCID 59909793HCID 59909793, compound

Product 2

HCID 222AmmoniaHCID 10270207HCID 10270207, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-N,N,5-trimethyl-1,3-oxazole-4-carboxamide (Preparation 73) (105 mg, 0.23 mmol) in ethanol (5 ml) was treated with 5% palladium on barium sulphate (45 mg) and ammonium formate (73 mg, 1.15 mmol) and the mixture was heated at 45° C. for 17 hours. Further palladium on barium sulphate (30 mg) and ammonium formate (60 mg, mmol) were added and the heating was continued for 2 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 foam (25 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-e640c3ff7a904cddb0fcae1023308299
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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