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

HRID 1730316Notes

Reaction equation

HRID 1730316 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.) isstirred 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 which is refluxed for an additional 2 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 hxane. 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 2 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. additionslowly added to an equal volume of hxane
  11. stirringThe resulting slurry is stirred for 15 minutes
  12. filtrationfiltered
  13. washThe filter cake is washed with hexane
  14. customair dried

Sources & evidence

ORD record
ord-03da952d1a824a93b00128137bd247a7
Source dataset
uspto-grants-1976_11
Patent number
US03992394

Reaction notes

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