Sodium Trifluoroacetate → 1-[[4-(hexahydro-1H-azepin-1-yl)-phenyl]-sulphonyl]-4-hydroxy-pyrrolidinon

HRID 1590590Notes

Reaction equation

HRID 1590590 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH2:18][CH:19]([OH:24])[CH2:20][C:21]([OH:23])=O)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C([O-])=O.[Na+]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]([S:14]([N:17]3[CH2:18][CH:19]([OH:24])[CH2:20][C:21]3=[O:23])(=[O:16])=[O:15])=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 517019Sodium TrifluoroacetateHCID 541188884-[[[4-(hexahydro-1H-azepin-1-yl)-phenyl]-sulphonyl]-amino]-3-hydroxy butanoic acid

Product 1

HCID 197675751-[[4-(hexahydro-1H-azepin-1-yl)-phenyl]-sulphonyl]-4-hydroxy-pyrrolidinon

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

6.3 g of the product obtained in Stage A above, 30 cm3 of trifluoroacetic anhydride and 6.3 g of sodium trifluoro-acetate are agitated under reflux for 12 hours. The mixture is evaporated to dryness, cooled down and the residue is taken up immediately in 120 cm3 of a 5% solution of sodium bicarbonate then in 350 cm3 of methanol. Agitation is carried out for 3 hours at ambient temperature, the mixture is concentrated to a reduced volume at 30° C. then extracted with methylene chloride, the extracts are dried and evaporated. The residue is chromatographed on silica (eluant: ethyl acetate - hexane (8-2)) after crystallization from ethanol, 2.1 g of desired product, M.p.=170-172° C., and 0.3 g of the corresponding delta-3,4 derivative are obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe mixture is evaporated to dryness
  3. temperaturecooled down
  4. concentrationthe mixture is concentrated to a reduced volume at 30° C.
  5. extractionthen extracted with methylene chloride
  6. customthe extracts are dried
  7. customevaporated
  8. customThe residue is chromatographed on silica (eluant: ethyl acetate - hexane (8-2))
  9. customafter crystallization from ethanol, 2.1 g of desired product, M.p.=170-172° C., and 0.3 g of the corresponding delta-3,4 derivative
  10. customare obtained

Sources & evidence

ORD record
ord-f44dbfdd988b43b0a7ca5d5f13d7ee37
Source dataset
uspto-grants-1993_04
Patent number
US05204341

Reaction notes

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