Acetone → HCID 178431949, compound

HRID 2163654Notes

Reaction equation

HRID 2163654 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 five minute period. The mixture is stirred for ten minutes after which the solvent is decanted from the tacky solid. 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%).

Workup

  1. stirringThe mixture is stirred for ten minutes after which the solvent
  2. customis decanted from the tacky solid
  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

Sources & evidence

ORD record
ord-8110a480b9d44e9fbdb81775c307d58f
Source dataset
uspto-grants-1979_01
Patent number
US04136096

Reaction notes

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