Sodium Methoxide → HCID 178428104, compound

HRID 49186Notes

Reaction equation

HRID 49186 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=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.C[O-].[Na+]>CO>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=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 10942334Sodium MethoxideHCID 178428105HCID 178428105, compound

Product 1

HCID 178428104HCID 178428104, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

(±)-7-(2-Chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (123.9 g) was suspended in methanol (1200 ml) and treated dropwise with a 28% solution of sodium methoxide in methanol (119.2 ml). The mixture was stirred at 50° C. for 30 minutes. The solvent was distilled off under reduced pressure, and the residue was combined with water and then the crystal was recovered by a filtration. The crystal was washed with water and dried to obtain (±)-7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (109.3 g) as a colorless crystal. To a solution of (±)-7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (109.3 g) in isopropyl alcohol (700 ml), a solution of L-pyroglutamic acid (10 g) in isopropyl alcohol (150 m) was added dropwise at 50° C. over a period of 1.5 hours. The mixture was stirred at 50° C. for 1 hour and then at room temperature for 2 days. The crystal was recovered by a filtration and washed with isopropyl alcohol to obtain (−)-7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (55.5 g, 88% ee). A recrystallization from ethanol resulted in an L-pyroglutamate (44.3 g, 97% ee). The crystal of the salt thus obtained was suspended in methanol (500 ml) and combined with a 28% methanol solution of sodium methoxide (10.9 ml). The mixture was stirred at 50° C. for 30 minutes and then the solvent was distilled off under reduced pressure. The crystal obtained was washed with water and dried to obtain (−)-7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (38.9 g). (This compound was proven to have an absolute configuration of an S form based in an X-ray crystal structure analysis.)

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. filtrationthe crystal was recovered by a filtration
  3. washThe crystal was washed with water
  4. customdried

Sources & evidence

ORD record
ord-b7b5a5b12e5a42ea91b9e251b7955d4d
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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