Trityl chloride → HCID 70605036, compound

HRID 1448368Notes

Reaction equation

HRID 1448368 reaction equation
[CH3:1][C:2]1([CH3:14])[S:6][C@@H:5]2[C@H:7]([NH2:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=O.[C:15]1([C:21](Cl)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.ClC(O[CH2:39][CH3:40])=O.COC1[CH:50]=[CH:49][C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:15]1([C:21]([NH:10][CH:7]2[C:8](=[O:9])[N:4]3[CH:3]([C:11](=[O:13])[NH:48][CH2:47][C:46]4[CH:49]=[CH:50][C:39]([CH3:40])=[CH:44][CH:45]=4)[C:2]([CH3:1])([CH3:14])[S:6][C@H:5]23)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 10928Ethyl chloroformateHCID 110826-Aminopenicillanic acidHCID 754524-Methoxybenzylamine

Product 1

HCID 70605036HCID 70605036, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

To a stirred slurry of 86.4 g. (0.4 mole) of 6-aminopenici llanic acid in 600 ml. of anhydrous chloroform is added 111.2 ml. (0.8 mole) of triethylamine, and the mixture is stirred at ambient temperature until a clear solution is obtained (ca. 15 minutes). To this solution is then added, portionwise over about 25 minutes, 134.9 g. (0.44 mole) of 90% pure triphenylmethyl chloride, at ambient temperature. Stirring is contained for a further 64 hours, and then 5.6 ml. of triethylamine is added. The solution is cooled to 0°-5° C., and then an ice-cold solution of 38 ml (0.4 mole) of ethyl chloroformate in 80 ml. of chloroform is added dropwise during 30 minutes with the reaction temperature being maintained between 4° and 9° C. After a further 15 minutes of stirring, 52.4 ml. (0.4 mole) of 4-methoxybenzylamine is injected into the reaction medium, below the surface of the solvent, at 4° and 9° C., and over a period of 30 minutes. Stirring is continued for a further 30 minutes at 3° to 6° C., for 20 minutes while the reaction medium warms to 20° C. The reaction mixture is then washed with water, followed by brine. Finally, it is dried using magnesium sulfate to give a chloroform solution of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-methylbenzyl]carbamoyl)penam

Workup

  1. customis obtained (ca. 15 minutes)
  2. additionTo this solution is then added, portionwise over about 25 minutes
  3. customat ambient temperature
  4. temperatureThe solution is cooled to 0°-5° C.
  5. temperaturebeing maintained between 4° and 9° C
  6. stirringAfter a further 15 minutes of stirring
  7. customis injected into the reaction medium, below the surface of the solvent, at 4° and 9° C.
  8. waitover a period of 30 minutes
  9. stirringStirring
  10. waitis continued for a further 30 minutes at 3° to 6° C., for 20 minutes while the reaction medium warms to 20° C
  11. washThe reaction mixture is then washed with water
  12. customFinally, it is dried

Sources & evidence

ORD record
ord-26a6bbdbf08847d988ad4525716c58ae
Source dataset
uspto-grants-1979_12
Patent number
US04179511

Reaction notes

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