Hydrochloric Acid → 6(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 1679625Notes

Reaction equation

HRID 1679625 reaction equation
C1C=CC=CC=1.[C:7]1([C:13]([NH:26][CH:27]2[C:37](=[O:38])[N:29]3[CH:30]([C:35]#[N:36])[C:31]([CH3:34])([CH3:33])[S:32][C@H:28]23)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N-:39]=[N+:40]=[N-:41].[Na+].Cl.C(N(CC)CC)C.Cl>O.C(Cl)(Cl)Cl>[C:7]1([C:13]([NH:26][CH:27]2[C:37](=[O:38])[N:29]3[CH:30]([C:35]4[NH:41][N:40]=[N:39][N:36]=4)[C:31]([CH3:34])([CH3:33])[S:32][C@H:28]23)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochloride2×HCID 33557Sodium Azide3×HCID 70604454HCID 70604454, compound

Product 1

HCID 1784319216(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A mixture of 6-triphenylmethylamino-2,2-dimethyl-3-cyanopenam benzene solvate, (258 mg., 0.5 mmole), sodium azide (33 mg. 0.5 mmole), triethylamine hydrochloride (69 mg., 0.5 mmole) and chloroform (10 ml.) is stirred and heated to reflux for three hours. Sodium azide (0.5 mmole) is then added to the mixture and refluxing continued overnight. One equivalent of each of sodium azide and triethylamine hydrochloride are added to the mixture is refluxed for an additional two hours. These additions are repeated twice more after which the mixture is again refluxed overnight. The mixture is cooled to room temperature and chloroform (10 ml.) added followed by water (10 ml.). The pH is adjusted to 2.0 with 6N hydrochloric acid, the mixture thoroughly mixed and the layers separated. The chloroform phase is washed with water (10 ml.) and is then seeded with a crystal from the product of Example 13. Crystallization occurs within five minutes. The slurry is stirred for ten minutes and then slowly added to an equal volume of hexane. The resulting slurry is stirred for 15 minutes and then filtered. The filter cake is washed with hexane and then air dried. Yield = 124 mg., 51.5%.

Workup

  1. temperatureheated
  2. temperatureto reflux for three hours
  3. temperaturerefluxing continued overnight
  4. temperatureis refluxed for an additional two hours
  5. additionthe mixture thoroughly mixed
  6. customthe layers separated
  7. washThe chloroform phase is washed with water (10 ml.)
  8. customCrystallization
  9. waitoccurs within five minutes
  10. stirringThe slurry is stirred for ten minutes
  11. additionslowly added to an equal volume of hexane
  12. stirringThe resulting slurry is stirred for 15 minutes
  13. filtrationfiltered
  14. washThe filter cake is washed with hexane
  15. customair dried

Sources & evidence

ORD record
ord-8c71b055cf6942b0a3c8caf67ce5c9de
Source dataset
uspto-grants-1978_03
Patent number
US04081455

Reaction notes

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