Acetic Acid → HCID 11088170, compound

HRID 1604085Notes

Reaction equation

HRID 1604085 reaction equation
C(O)(=O)C.C([O:9][C:10](=O)[CH2:11][CH2:12][CH:13]([OH:31])[C@@H:14]([N:16]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:15])(C)(C)C.C([O-])(O)=O.[Na+]>CS(O)(=O)=O.C1(C)C=CC=CC=1>[CH2:17]([N:16]([C@H:14]([C@H:13]1[O:31][C:10](=[O:9])[CH2:11][CH2:12]1)[CH3:15])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 22868420HCID 22868420, compound

Product 1

HCID 11088170HCID 11088170, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 1140TolueneSolvent

Procedure

Glacial acetic acid (0.4 mL) and one drop of methanesulfonic acid were added to a solution of (5S)-5-(N,N-dibenzylamino)-4-hydroxy-hexanoic acid-tert-butyl ester (0.6 g, 1.57 mmol) in dry toluene (15.0 mL) in a 50 mL round bottom flask fitted with a reflux condenser. The reaction mixture was heated at reflux for 12 hours and then cooled to ambient temperature. The pH of the solution was adjusted to 7 by slow addition of a saturated solution of NaHCO3. The organic layer was separated, and the aqueous layer was extracted with Et2O (10 mL). The combined organic extracts were dried over MgSO4, filtered, and the solvent was removed in vacuo. The residue thus obtained was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to obtain 0.41 g (85% yield) of pure (5S)-5[(1S)-1-(N,N-dibenzylamino)-ethyl]-dihydrofuran-2(3H)-one (5a). White solid, mp. 61-62° C., 1H NMR (300.15) δ 1-11 (d, J=6.6 Hz, 3 H), 1.83-2.15 (m, 2 H), 2.44-2.50 (m, 2 2.86 (pentet, J=6.9 Hz, 1 H), 3.71 (ABq, δA =3.87, δB =3.56, JAB=13.8 Hz, 4 H), 4.49 (pentet, J=7.2 Hz, 1 H), 7.10-7.41 (m, 10 H); 13C NMR (75.8 MHz) 10.9, 25.6, 28.7, 54.3, 55.8, 83.1, 126.8, 128.2, 128.7, 139.9, 177.1; MS (10W res.) 310 (M+1, 20%), 224 (MeCHNBn2, 40%), 91 (NBn2, 100%); HRMS for C20H24NO2 : 310.1807 (calc'd 310.1801); Anal calc'd for C20H23NO2 : C 77.64, H 7.49, N 4.53; Found: 77.54, H 7.55, N 4.49.

Workup

  1. customfitted with a reflux condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 12 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with Et2O (10 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe residue thus obtained
  10. customwas purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-0e75c698cbb64b919c0ba29519218791
Source dataset
uspto-grants-1999_11
Patent number
US05990341

Reaction notes

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