Acetone → HCID 178431949, compound

HRID 1731223Notes

Reaction equation

HRID 1731223 reaction equation
CC(C)=O.C1(C([NH:24][CH:25]2[C:38](=[O:39])[N:27]3[CH:28]([C:33]4[NH:37][N:36]=[N:35][N:34]=4)[C:29]([CH3:32])([CH3:31])[S:30][C@H:26]23)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[NH2:24][CH:25]1[C:38](=[O:39])[N:27]2[CH:28]([C:33]3[NH:34][N:35]=[N:36][N:37]=3)[C:29]([CH3:31])([CH3:32])[S:30][C@H:26]12

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 1784319216(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

Product 1

HCID 178431949HCID 178431949, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a slurry of dry acetone (5 ml.) and 6-triphenylmethylamino-2,2-dimethyl-3-(5-tetrazolyl)penam (483 mg., 1.0 mmole) at room temperature is added p-toluenesulfonic acid monohydrate (209 mg., 1.1 mmole). The resulting solution is stirred for 10 minutes and then ether (30 ml.) is added over a 5 minute period. The mixture is stirred for 10 minutes after which the solvent is decanted from the solid which separates. The solid is dissolved in tetrahydrofuran (30 ml.) and placed on a column (300 × 6 mm.) packed with 10 g. of Florisil (synthetic magnesium silicate). The column is washed with tetrahydrofuran until a total of 125 ml. is collected. The eluate is concentrated to dryness under reduced pressure at 40° C. to give 210 mg. of solid. The solid is slurried in ether (30 ml.), filtered, washed with ether and air-dried. Yield = 121 mg. (50%). The NMR spectrum (in DMSO-d6) shows absorption bands at 1.08 ppm, (2s, 3H each, C-2 methyls), 4.60 + 5.52 (2d, J=4.0 Hz, 2H, H5 + H6), 5.10 (s, 1H H3) and 5.88 (s, 3H, NH3)ppm. (s, 3H), 1.59ppm (s,3H), 4.60 ppm (d,1H), 5.52 ppm (d,1H), 5.10ppm (s, 1H), and 5.88 ppm (s,3H).

Workup

  1. stirringThe mixture is stirred for 10 minutes after which the solvent
  2. customis decanted from the solid which
  3. dissolutionThe solid is dissolved in tetrahydrofuran (30 ml.)
  4. washThe column is washed with tetrahydrofuran until a total of 125 ml
  5. customis collected
  6. concentrationThe eluate is concentrated to dryness under reduced pressure at 40° C.
  7. customto give 210 mg
  8. filtrationfiltered
  9. washwashed with ether
  10. customair-dried
  11. customabsorption bands at 1.08 ppm

Sources & evidence

ORD record
ord-497e846a7c8748c7a6ae5335454642a6
Source dataset
uspto-grants-1976_11
Patent number
US03994939

Reaction notes

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