Allyltributylstannane → HCID 86728130, compound

HRID 627661Notes

Reaction equation

HRID 627661 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[C@@:16]1([CH3:41])[N:21]=[C:20]([N:22]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:19]([CH3:38])([CH3:37])[S:18](=[O:40])(=[O:39])[CH2:17]1)(=O)=O.O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)[C:45]1[CH:50]=CC=C[C:46]=1P(C1C=CC=CC=1)C1C=CC=CC=1.C([Sn](CCCC)(CCCC)CCCC)C=C>CC#N.CC#N.Cl[Pd]Cl.CN(C=O)C>[C:26]([O:25][C:23](=[O:24])[N:22]([C:20]1[C:19]([CH3:37])([CH3:38])[S:18](=[O:40])(=[O:39])[CH2:17][C@:16]([C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[CH2:50][CH:45]=[CH2:46])([CH3:41])[N:21]=1)[C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 86728129HCID 86728129, compound

Product 1

HCID 86728130HCID 86728130, compoundYield 468.5%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

100 ml RBF was charged with (R)-2-(5-((bis-(tert-butoxycarbonyl))amino)-3,6,6-trimethyl-1,1-dioxido-3,6-dihydro-2H-1,4-thiazin-3-yl)-4-nitrophenyl trifluoromethanesulfonate (794 mg, 1.204 mmol), bis(acetonitrile)palladium(II)dichloride (31.2 mg, 0.120 mmol), (oxydi-2,1-phenylene)bis(diphenylphosphine) (130 mg, 0.241 mmol) and DMF (6 ml). The mixture was stirred for 2 min until all solids dissolved. Allyltri-n-butylstannane (0.746 ml, 2.407 mmol) was added, the vial was sealed and stirred at 75° C. (heating block) for 30 min. The mixture was concentrated in vacuo and purified by FC on 40 g RediSep Gold column using 5-70% EtOAc in heptane to afford (R)-tert-butyl-N-(5-(2-allyl-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxycarbonyl-carbamate (623 mg, 1.129 mmol, 94% yield). LC/MS (ESI+) m/z=574 (M+Na).

Workup

  1. dissolutiondissolved
  2. customthe vial was sealed
  3. stirringstirred at 75° C.
  4. temperature(heating block) for 30 min
  5. concentrationThe mixture was concentrated in vacuo
  6. custompurified by FC on 40 g RediSep Gold column

Sources & evidence

ORD record
ord-5322443c3d5f4d1f922a90c7aa351cef
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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