L-Pyroglutamic Acid → HCID 178428106, compound

HRID 49187Notes

Reaction equation

HRID 49187 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=[N:19][NH:20][C:21]([NH2:23])=[NH:22])[CH2:9]1.[NH:24]1[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C:30]([OH:32])=[O:31]>C(O)(C)C>[NH:24]1[C:28](=[O:29])[CH2:27][CH2:26][C@H:25]1[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:17][C:16]2[N:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=2[C:10](=[N:19][NH:20][C:21]([NH2:23])=[NH:22])[CH2:9]1

Participants

4

Reactant 2

HCID 7405L-Pyroglutamic AcidHCID 178428104HCID 178428104, compound

Product 1

HCID 178428106HCID 178428106, compoundYield 156.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

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. waitat room temperature for 2 days
  2. filtrationThe crystal was recovered by a filtration
  3. washwashed with isopropyl alcohol

Sources & evidence

ORD record
ord-86f15724d40c4e48a0e6e4a8c37af702
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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