HCID 59625608, compound → HCID 59625517, compound

HRID 2192830Notes

Reaction equation

HRID 2192830 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:20]2[CH2:25][C@@H:24]([NH:26]C(OCC(Cl)(Cl)Cl)=O)[CH2:23][N:22]([C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:36])[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Cu].[Zn]>[NH2:26][C@@H:24]1[CH2:25][C@H:20]([N:19]([C:17]([C:8]2[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[N:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6][CH:7]=2)=[O:18])[CH2:45][CH:46]([CH3:48])[CH3:47])[CH2:21][N:22]([C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36])[CH2:23]1

Participants

4

Reactant 1

HCID 59625608HCID 59625608, compound

Product 1

HCID 59625517HCID 59625517, compound

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of benzyl (3S,5R)-3-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-{[(2,2,2-trichloroethoxy)carbonyl]amino}piperidine-1-carboxylate (550% mg) in acetic acid (14 ml) was added zinc-copper couple (200 mg) and the mixture was stirred at room temperature for 3 hr. Insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the mixture was concentrated under reduced pressure. The obtained residue was diluted with saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object compound (420 mg).

Workup

  1. filtrationInsoluble material was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionToluene was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe obtained residue was diluted with saturated aqueous sodium hydrogen carbonate solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-09ae0fd94d6d4051880d828d7c39df13
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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