Acetic Acid → HCID 18374574, compound

HRID 2300703Notes

Reaction equation

HRID 2300703 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:39]2[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[CH:41][CH:40]=2)[CH:10]([C:25](N2C(C3C=CC=CC=3)COC2=O)=[O:26])[CH2:11][CH2:12][CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:14][Si](C)(C)C)=[CH:4][CH:3]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>COC(C)(C)C.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:25](=[O:26])[CH:10]([CH2:11][CH2:12][CH:13]([OH:14])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:9]2[C:39]2[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[CH:41][CH:40]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 18374602HCID 18374602, compound

Product 1

HCID 18374574HCID 18374574, compound

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 11708267BistrimethylsilylacetamidSolvent

Procedure

2.7 g of 4-[1-(4-fluorophenylamino)-2-(2-oxo-4-phenyloxazolidine-3-carbonyl)-5-phenyl-5-trimethylsilanyloxypentyl]benzonitrile in 30 ml of tert-butyl methyl ether, 1.6 ml of bistrimethylsilylacetamide and 0.2 g of tetrabutylammonium fluoride trihydrate are heated at reflux for 3 hours. The mixture is allowed to stand overnight, 0.2 ml of glacial acetic acid are added, and the mixture is stirred for 15 min and then substantially concentrated. 15 ml of a mixture of isopropanol/2N sulfuric acid=10:1 are added, and the mixture is stirred at room temperature for 1 hour. The mixture is then treated with a little solid sodium bicarbonate and again substantially concentrated and the residue is taken up in ethyl acetate and washed with water. The residue of the dried organic phase is purified by column filtration (SiO2, ethyl acetate/n-heptane=1:1). This gives the product of molecular weight 400.5 (C25H21FN2O2); MS (DCl+): 401 (M+H+), 383 (M+H+−H2O).

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationsubstantially concentrated
  3. addition15 ml of a mixture of isopropanol/2N sulfuric acid=10:1 are added
  4. stirringthe mixture is stirred at room temperature for 1 hour
  5. additionThe mixture is then treated with a little solid sodium bicarbonate
  6. concentrationagain substantially concentrated
  7. washwashed with water
  8. filtrationThe residue of the dried organic phase is purified by column filtration (SiO2, ethyl acetate/n-heptane=1:1)
  9. customThis gives the product of molecular weight 400.5 (C25H21FN2O2)

Sources & evidence

ORD record
ord-cb27267bf09f43daba57de1f3697293c
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

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