Formic Acid → HCID 73678510, compound

HRID 1451551Notes

Reaction equation

HRID 1451551 reaction equation
[CH2:1]([O:8][N:9]=[C:10]1[CH2:19][CH2:18][CH:17]([O:20][C:21](=[O:26])[CH:22]([CH3:25])[CH2:23][CH3:24])[CH:16]2[C:11]1=[CH:12][C:13](=[O:42])[CH:14]([CH3:41])[CH:15]2[CH2:27][CH2:28][C:29](=[O:40])[CH2:30][CH:31]([OH:39])[CH2:32][C:33]([O:35]CC=C)=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)=O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][N:9]=[C:10]1[CH2:19][CH2:18][CH:17]([O:20][C:21](=[O:26])[CH:22]([CH3:25])[CH2:23][CH3:24])[CH:16]2[C:11]1=[CH:12][C:13](=[O:42])[CH:14]([CH3:41])[CH:15]2[CH2:27][CH2:28][C:29](=[O:40])[CH2:30][CH:31]([OH:39])[CH2:32][C:33]([OH:35])=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 11776TriphenylphosphineHCID 73678513HCID 73678513, compound

Product 1

HCID 73678510HCID 73678510, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

239 mg (0.4 mmole) of allyl 7-[5-benzyloxyimino-2-methyl-8-(2-methylbutyryloxy)-3-oxo-1,2,3,5,6,7,8,8a-octahydro-1-naphthyl]-3-hydroxy-5-oxoheptanoate (prepared as described in Example 1a) were dissolved in 3.3 ml of anhydrous tetrahydrofuran, and 20.7 mg (0.02 mmole) of tetrakis(triphenylphosphine)palladium (0), 21.5 mg (0.08 mmole) of triphenylphosphine and 31 μl (0.82 mmole) of formic acid were added to the solution, and the resulting mixture was stirred for 18 hours under an atmosphere of nitrogen. At the end of this time, the reaction mixture was condensed by evaporation under reduced pressure, and the residue was dissolved in a 50% v/v aqueous solution of acetonitrile. The solution was filtered through a SEP-PAK C-18 Cartridge (Trade name for a product of Waters Co.) and extracted with ethyl acetate. The resulting ethyl acetate extract was dried over anhydrous magnesium sulfate, filtered and condensed by evaporation under reduced pressure. The resulting oily residue was purified through a reverse phase Lobar Column (RP-18, Size B, Merck), using as the eluent a buffer solution consisting of a 1:1 by volume mixture of acetonitrile and aqueous phosphoric acid (pH 3.0) containing 0.001M of triethylamine, to obtain 106 mg (yield 48%) of the title compound as an oily substance.

Workup

  1. customcondensed
  2. customby evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in a 50% v/v aqueous solution of acetonitrile
  4. filtrationThe solution was filtered through a SEP-PAK C-18 Cartridge (Trade name for a product of Waters Co
  5. extraction) and extracted with ethyl acetate
  6. extractionThe resulting ethyl acetate extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customcondensed
  10. customby evaporation under reduced pressure
  11. customThe resulting oily residue was purified through a reverse phase Lobar Column (RP-18, Size B, Merck)
  12. additionconsisting of a 1:1 by volume mixture of acetonitrile and aqueous phosphoric acid (pH 3.0)
  13. additioncontaining 0.001M of triethylamine

Sources & evidence

ORD record
ord-63a445110ac5489798c0bc0f7ce3fe3b
Source dataset
uspto-grants-1997_02
Patent number
US05604256

Reaction notes

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