Sulfuric Acid → HCID 22618794, compound

HRID 617573Notes

Reaction equation

HRID 617573 reaction equation
O[C:2]1([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.S(=O)(=O)(O)O.C(=O)([O-])[OH:26].[Na+].[C:30](#[N:32])[CH3:31]>>[C:30]([NH:32][C:2]1([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1)(=[O:26])[CH3:31]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 22618750HCID 22618750, compound

Product 1

HCID 22618794HCID 22618794, compound

Procedure

To a solution of 8-hydroxy-8-(2-phenylethyl)-1,4-dioxaspiro[4.5]decane (12.8 g) in acetonitrile (200 ml), a concentrated sulfuric acid (5.7 ml) was dropwise added under ice-cooling over 3 minutes. The reaction mixture was left standing at room temperature for 2 days, poured into a saturated aqueous sodium hydrogencarbonate solution under ice-cooling and extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure to give 8-acetamido-8-(2-phenylethyl)-1,4-dioxaspiro[4.5]decane as a crude product. The crude product was dissolved in tetrahydrofuran (140 ml) without purifying and thereto was added a 0.1N aqueous hydrochloric acid solution (30 ml) at room temperature and the mixture was allowed to stand overnight. The mixture was carefully poured into a ice-cooled saturated aqueous sodium hydrogen-carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled away to give crude crystals. The crystals were recrystallized from a mixed solvent (1:1) of 1,2-dimethoxyethane-diisopropyl ether to give 1/5 hydrate of the subject compound (5.1 g) as white crystals, melting at 140-143° C.

Workup

  1. temperaturecooling over 3 minutes
  2. waitThe reaction mixture was left
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materiala saturated brine and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-a1188bf908fa453fb044c82d250f980e
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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