L-Pyroglutamic Acid → HCID 178428134, compound

HRID 49200Notes

Reaction equation

HRID 49200 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:20][NH:21][C:22]([NH2:24])=[NH:23])[CH2:10]1.[NH:25]1[C:29](=[O:30])[CH2:28][CH2:27][C@H:26]1[C:31]([OH:33])=[O:32]>C(O)C>[NH:25]1[C:29](=[O:30])[CH2:28][CH2:27][C@H:26]1[C:31]([OH:33])=[O:32].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:20][NH:21][C:22]([NH2:24])=[NH:23])[CH2:10]1

Participants

4

Reactant 2

HCID 7405L-Pyroglutamic AcidHCID 178428132HCID 178428132, compound

Product 1

HCID 178428134HCID 178428134, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (7.1 g) in ethanol (85 ml) was combined with L-pyroglutamic acid (2.72 g) and heated to form a uniform solution. The mixture was allowed to stand to cool gradually, and stirred at room temperature for 14 hours. The crystal precipitated was recovered by a filtration and washed with ethanol to obtain (+)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (4.1 g). This crystal was suspended in methanol (50 ml) and combined with a 28% solution of sodium methoxide in methanol (1.7 g) and then the solvent was distilled off under reduced pressure. The resultant crystal was washed with water and dried to obtain a crystal (3.1 g). This was dissolved in ethanol (20 ml) and combined with methanesulfonic acid (1.8 g). The solvent was distilled off under reduced pressure, and the resultant crystal was recrystallized from ethanol to obtain (+)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound H)(3.6 g, 99.3% ee).

Workup

  1. temperatureheated
  2. customto form a uniform solution
  3. temperatureto cool gradually
  4. customThe crystal precipitated
  5. filtrationwas recovered by a filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-f22373ef009c4ad394520835f6116971
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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