Hexane → HCID 54284810, compound

HRID 1682435Notes

Reaction equation

HRID 1682435 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:38](=[O:39])[N:13]3[C:14]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)=[O:27])=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Sn](CCCC)(CCCC)[C:45]1[O:46][CH2:47][CH2:48][CH:49]=1)CCC.CCCCCC>CN1CCCC1=O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[O:46]1[CH2:47][CH2:48][CH:49]=[C:45]1[C:15]1[CH2:16][S:17][C@@H:12]2[C@H:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:38](=[O:39])[N:13]2[C:14]=1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)=[O:27]

Participants

7

Reactant 3

HCID 8058HexaneHCID 10769651HCID 10769651, compoundHCID 14323397Tributyl(2,3-dihydrofuran-5-yl)stannane

Product 1

HCID 54284810HCID 54284810, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8857Ethyl AcetateSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-Methoxybenzyl (6R,7R)-7-phenylacetamido-3-trifluoromethane-sulphonyloxyceph-3-em-4-carboxylate (0.10 g), bis(dibenzylideneacetone)-palladium (0) (0.003 g) and tri-n-butyl(4,5-dihydrofuran-2-yl)stannane (0.122 g, 0.108 ml ) in dry N-methylpyrrolidinone (0.5 ml) were stirred together for 0.25 h. T.l.c. analysis (50% ethyl acetate--hexane) showed no starting material. The mixture was diluted with ethyl acetate, washed three times with water and with brine and then dried. The solution was concentrated to a small volume and then added dropwise to vigorously stirred hexane (50 ml). The suspension was centrifuged and the clear hexane decanted. The precipitate was washed with hexane and dried in vacuo, to give the title compound as a buff coloured, amorphous solid (0.08 g, 93%); δH (250 MHz, CDCl3) 2.60 (2H, dt, J 9.8, 2.9 Hz), 3.38 and 3.47 (2H, ABq, J 18.1 Hz), 3.60 and 3.96 (2H, ABq, J 16.2 Hz), 3.80 (3H, s), 4.07 (1H, dt, J 18.6, 9.8 Hz), 4.21 (1H, dt, J 17.9, 8.5 Hz), 4.94 (1H, d, J 4.9 Hz), 5.02 (1H, t, 2.9 Hz), 5.17 and 5.23 (2H, ABq, J 12.0 Hz), 5.82 (1H, dd, J 9.1, 4.8 Hz), 6.01 (1H, d, J9.1 Hz), 6.88 (2H, d, J 8.7 Hz) and 7.25-7.41 (7H, m).

Workup

  1. washwashed three times with water
  2. dry with materialwith brine and then dried
  3. concentrationThe solution was concentrated to a small volume
  4. additionadded dropwise to vigorously stirred hexane (50 ml)
  5. customthe clear hexane decanted
  6. washThe precipitate was washed with hexane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d3da0ad64a264abfaa85af40cc5841ae
Source dataset
uspto-grants-1997_06
Patent number
US05635501

Reaction notes

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