5-Methyl-2-(tri-n-butylstannyl)pyridine → tert-butyl (4S,5S)-4-benzyl-5-{2-{[(benzyloxy)carbonyl]amino}-3-[4-(5-methyl-2-pyridinyl)phenyl]propyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1174333Notes

Reaction equation

HRID 1174333 reaction equation
[CH2:1]([C@H:8]1[C@H:12]([CH2:13][CH:14]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:15][C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[O:11][C:10]([CH3:35])([CH3:34])[N:9]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:43][C:44]1[CH:45]=[CH:46][C:47]([Sn](CCCC)(CCCC)CCCC)=[N:48][CH:49]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C@H:8]1[C@H:12]([CH2:13][CH:14]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:47]3[CH:46]=[CH:45][C:44]([CH3:43])=[CH:49][N:48]=3)=[CH:18][CH:17]=2)[O:11][C:10]([CH3:35])([CH3:34])[N:9]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 67406532tert-butyl (4S,5S)-4-benzyl-5-[2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 67407093tert-butyl (4S,5S)-4-benzyl-5-{2-{[(benzyloxy)carbonyl]amino}-3-[4-(5-methyl-2-pyridinyl)phenyl]propyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylateYield 63.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 128B (0.50 g, 0.78 mmol) in DMF (8 mL) was treated with dichlorobis(triphenylphosphine)palladium(II) (0.165 g, 0.235 mmol), and the product from Example 74A (0.60 g, 1.63 mmol), stirred at 100° C. for 6 hours, cooled to 25° C., filtered through celite®, and partitioned between ethyl acetate and water. The organic was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-15% ethyl acetate in chloroform to give the product (0.322 g, 63% yield).

Workup

  1. filtrationfiltered through celite®
  2. custompartitioned between ethyl acetate and water
  3. washThe organic was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 0-15% ethyl acetate in chloroform

Sources & evidence

ORD record
ord-f9d0603e86434099ab357f965bf24485
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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