Anisole → HCID 20223240, compound

HRID 980022Notes

Reaction equation

HRID 980022 reaction equation
CS(O)(=O)=O.C(OC([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]([O:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:34](=[NH:36])[NH2:35])[CH:30]=2)[CH:25]=1)=[O:22])=O)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[BrH:45].C(O)(=O)C>C(O)(=O)C>[BrH:45].[BrH:45].[NH:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]([O:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:34](=[NH:35])[NH2:36])[CH:30]=2)[CH:25]=1)=[O:22]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86741200HCID 86741200, compound

Product 1

HCID 20223240HCID 20223240, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.5 g of 6-amidino-2-naphthyl 1-benzyloxycarbonylpyrrolidine-2-carboxylate methanesulfonate in 10 ml of acetic acid, was added 1 ml of anisole. To the mixture, while cooling in ice and stirring, was added 3 ml of a 30% HBr/acetic acid solution. Thereafter the resulting mixture was stirred overnight at room temperature. The precipitate was collected by filtration and washed sufficiently with ethyl ether and acetone. Recrystallization from a mixture of methanol and ethyl ether gave 1.1 g of 6-amidino-2-naphthyl pyrrolidine-2-carboxylate dihydrobromide.

Workup

  1. temperatureTo the mixture, while cooling in ice
  2. stirringThereafter the resulting mixture was stirred overnight at room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed sufficiently with ethyl ether and acetone
  5. customRecrystallization
  6. additionfrom a mixture of methanol and ethyl ether

Sources & evidence

ORD record
ord-0f395d723b514f998acd2f1e6db2b3e2
Source dataset
uspto-grants-1987_01
Patent number
US04634783

Reaction notes

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