Ethanol → tert-Butyl 2-(3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)butanoate

HRID 7297Notes

Reaction equation

HRID 7297 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@@H:16]1[CH2:20][CH2:19][N:18]([C@H:21]([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]1=[O:30])(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH2:31](O)C.C(NC(C)C)(C)C>[Pd].C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][CH:16]1[CH2:20][CH2:19][N:18]([CH:21]([CH2:29][CH3:31])[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:17]1=[O:30])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 702EthanolHCID 7912DiisopropylamineHCID 69222335tert-Butyl(2R)-2-((3R)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

Product 1

HCID 22017281tert-Butyl 2-(3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of Intermediate 112 [Mixture 1] (0.051 g), 10% palladium on carbon (0.01 g) and ethanol (5 ml) was stirred under an atmosphere of hydrogen for 18 h. The reaction mixture was filtered through Celite™ and the filtrate was concentrated under reduced pressure to give a yellow gum. The gum (0.034 g) in DCM (2 ml) was treated with 6-chloronaphthylsulphonyl chloride1 (0.04 g) and N,N-diisopropylamine (0.073 ml) and stirred at room temperature for 24 h. The mixture was washed with water and concentrated under reduced pressure to yield an oil which was partially purified using SPE (silica, eluting with cyclohexane:ethyl acetate 1:1) to give the title compound (0.043 g) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a yellow gum
  4. stirringstirred at room temperature for 24 h
  5. washThe mixture was washed with water
  6. concentrationconcentrated under reduced pressure
  7. customto yield an oil which
  8. customwas partially purified
  9. washSPE (silica, eluting with cyclohexane:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-11adef3129b84f0b94db91599fbd1023
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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