Tetramethyltin → HCID 66968780, compound

HRID 1255519Notes

Reaction equation

HRID 1255519 reaction equation
C[Sn](C)(C)C.[Cl-].[Li+].[C:8]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:28]1[CH:29]=[CH:30][C:31]2[C:32](=[O:70])[N:33]3[CH2:54][CH:53]=[CH:52][CH2:51][CH2:50][C@@H:49]4[CH2:55][CH2:56][CH2:57][C@H:48]4[O:47][C:46](=[O:58])[NH:45][C@@H:44]([CH:59]4[CH2:63][CH2:62][CH2:61][CH2:60]4)[C:43](=[O:64])[N:42]4[CH2:65][C@@H:39]([CH2:40][C@H:41]4[C:66]([O:68][CH3:69])=[O:67])[O:38][C:34]3=[N:35][C:36]=2[CH:37]=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>[CH3:69][O:68][C:66]([C@@H:41]1[CH2:40][C@@H:39]2[CH2:65][N:42]1[C:43](=[O:64])[C@H:44]([CH:59]1[CH2:60][CH2:61][CH2:62][CH2:63]1)[NH:45][C:46](=[O:58])[O:47][C@@H:48]1[CH2:57][CH2:56][CH2:55][C@H:49]1[CH2:50][CH2:51][CH:52]=[CH:53][CH2:54][N:33]1[C:32](=[O:70])[C:31]3[CH:30]=[CH:29][C:28]([CH3:8])=[CH:37][C:36]=3[N:35]=[C:34]1[O:38]2)=[O:67]

Participants

7

Reactant 4

HCID 11661TetramethyltinHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 66968577HCID 66968577, compound

Product 1

HCID 66968780HCID 66968780, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Tetramethyltin (0.041 ml, 0.298 mmol), lithium chloride (50.5 mg, 1.191 mmol), triphenylphosphine (15.62 mg, 0.060 mmol) and bis(triphenylphosphine)palladium(II) chloride (15.68 mg, 0.022 mmol) were added to a nitrogen purged solution of methyl (3aR,7S,10S,12R,22E,25aS)-16-bromo-7-cyclopentyl-5,8,19-trioxo-1,2,3,3a,5,6,7,8,11,12,21,24,25,25a-tetradecahydro-10H,19H-9,12-methanocyclopenta[18,19][1,10,3,6,12]dioxatriazacyclononadecino[11,12-b]quinazoline-10-carboxylate, Example 59 Step 1 (100 mg, 0.149 mmol) in DMF (2 ml). The mixture was heated to 90° C. for 3 hr. The reaction was diluted with aqueous. KHSO4 and product extracted into ethyl acetate. The organic extract was washed with aqueous sodium bicarbonate, dried over sodium sulfate, filtered, concentrated and chromatographed on silica using 20-50% ethyl acetate/hexane to give the title compound as a foam, (74 mg, 82%). LCMS (ES+) m/z 607.3 (M+H)+.

Workup

  1. additionThe reaction was diluted with aqueous
  2. extractionKHSO4 and product extracted into ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica using 20-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f8e2b938180f49218bdc8e7c8e124187
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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