Triphenylarsine → HCID 178484164, compound

HRID 1158626Notes

Reaction equation

HRID 1158626 reaction equation
C[C@]1(O)[C@@H]2C(=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]3C2)C(=O)C2C(O)=CC=CC1=2.[CH3:33][N:34]([CH3:73])[C@H:35]1[C@H:52]2[C@:39]([OH:67])([C:40]([OH:66])=[C:41]3[C@H:50]([CH2:51]2)[CH2:49][C:48]2[C:43](=[C:44]([OH:64])[C:45]([NH:54][C:55](=[O:63])[CH2:56][N:57]4[CH2:62][CH2:61][CH2:60][CH2:59][O:58]4)=[CH:46][C:47]=2I)[C:42]3=[O:65])[C:38](=[O:68])[C:37]([C:69]([NH2:71])=[O:70])=[C:36]1[OH:72].C1C=CC([As](C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([Sn](CCCC)(CCCC)[C:98]1[S:99][CH:100]=[CH:101][CH:102]=1)CCC>C1(C)C=CC=CC=1.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.[Cu]I>[CH3:33][N:34]([CH3:73])[C@H:35]1[C@H:52]2[C@:39]([OH:67])([C:40]([OH:66])=[C:41]3[C@H:50]([CH2:51]2)[CH2:49][C:48]2[C:43](=[C:44]([OH:64])[C:45]([NH:54][C:55](=[O:63])[CH2:56][N:57]4[CH2:62][CH2:61][CH2:60][CH2:59][O:58]4)=[CH:46][C:47]=2[C:98]2[S:99][CH:100]=[CH:101][CH:102]=2)[C:42]3=[O:65])[C:38](=[O:68])[C:37]([C:69]([NH2:71])=[O:70])=[C:36]1[OH:72]

Participants

8

Reactant 4

HCID 11773TriphenylarsineHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 178418840HCID 178418840, compoundHCID 178484165HCID 178484165, compound

Product 1

HCID 178484164HCID 178484164, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst2×HCID 1140TolueneSolvent

Procedure

A mixture of 40 mg of Example 9 (4S,4aS,5aR,12aS)-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-9-[(1,2-oxazinan-2-ylacetyl)amino]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, 6 mg Pd(PPh3)2Cl2 (dichlorobis(triphenyl-phosphine)palladium(II), 2 mg AsPh3, 2 mg Cul (copper(1) iodide) and 2-(tributylstannyl)-thiophene in 10 mL toluene is heated to reflux under nitrogen for ca. 6 h. The reaction mixture is cooled, filtered and solvent removed. The crude residue is dissolved in water at pH 2 (by adding 10% HCl), and 10% ammonium hydroxide is added to adjust the pH to about 4 followed by extraction with methylene chloride. Organic layer dried over sodium sulfate, solvent removed and residue triturated with ether and 1M HCl in ether to give 8 mg of the product of the example.

Workup

  1. temperatureis heated
  2. temperatureto reflux under nitrogen for ca. 6 h
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. customsolvent removed
  6. dissolutionThe crude residue is dissolved in water at pH 2 (by adding 10% HCl), and 10% ammonium hydroxide
  7. additionis added
  8. extractionfollowed by extraction with methylene chloride
  9. dry with materialOrganic layer dried over sodium sulfate, solvent
  10. customremoved
  11. customresidue triturated with ether and 1M HCl in ether

Sources & evidence

ORD record
ord-73f3603056564e57aa3bca917b9ebedc
Source dataset
uspto-grants-2010_10
Patent number
US07812008B2

Reaction notes

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