Acetone → HCID 178431949, compound

HRID 1730321Notes

Reaction equation

HRID 1730321 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 andthen ether (30 ml.) is added over a five minute period. The mixture is stirred for ten minutes after which the solvent is decanted from the tackysolid. 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 underreduced 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%).

Workup

  1. additionis added over a five minute period
  2. customis decanted from the tackysolid
  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 underreduced pressure at 40° C.
  7. customto give 210 mg
  8. filtrationfiltered
  9. washwashed with ether
  10. customair-dried

Sources & evidence

ORD record
ord-41534fbd322246c99e5847db9944882c
Source dataset
uspto-grants-1976_11
Patent number
US03992394

Reaction notes

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