Ammonium formate → HCID 86598961, compound

HRID 2220434Notes

Reaction equation

HRID 2220434 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:43])[CH2:9][N:10]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[O:33])=[C:28]([NH:39][CH:40]([CH3:42])[CH3:41])[CH:27]=3)=[CH:22][CH:21]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>CO.O.[Pd].C(Cl)(Cl)Cl>[OH:43][C@H:8]([C:5]1[CH:6]=[N:7][CH:2]=[CH:3][CH:4]=1)[CH2:9][N:10]([CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH:34][S:35]([CH3:38])(=[O:36])=[O:37])=[O:33])=[C:28]([NH:39][CH:40]([CH3:42])[CH3:41])[CH:27]=2)=[CH:24][CH:25]=1)[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 86598962HCID 86598962, compound

Product 1

HCID 86598961HCID 86598961, compoundYield 98.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl [(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl][2-[3′-(isopropylamino)-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]ethyl]-carbamate (132 mg) in methanol (3.0 ml) and water (0.30 ml) were added ammonium formate (66 mg) and palladium on carbon (66 mg) at room temperature. The mixture was stirred under reflux for 1 hour. The suspension was cooled to room temperature, diluted with chloroform and filtrated. The filtrate was concentrated in vacuo and the residue was dissolved with chloroform, methanol and water. The organic layer was separated, and the aqueous layer was extracted with chloroform and methanol twice. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give tert-butyl [(2R)-2-hydroxy-2-(3-pyridyl)ethyl][2-[3′-(isopropylamino)-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]ethyl]-carbamate (123 mg).

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationfiltrated
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved with chloroform, methanol and water
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform and methanol twice
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43f7d5cc10724748acddcd1e963023da
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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