L-Pyroglutamic Acid → HCID 178428106, compound

HRID 1700585Notes

Reaction equation

HRID 1700585 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

To a solution of (±)-7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (109.3 g) in isopropylalcohol (700 ml) was added dropwise a solution of L-pyroglutamic acid (10 g) in isopropylalcohol (700 ml) at 50° C. for 1.5 hours, and the mixture was stirred at 50° C. for 1 hour and then at room temperature for 2 days. The crystals were filtered and washed with isopropylalcohol to give (−)-7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (55.5 g, 88%ee), which was recrystallized from ethanol to give crystals of L-pyroglutamate (44.3 g, 97%ee). The thus obtained crystals of salt was suspended in methanol (500 ml), and to the suspension was added a solution of 28% sodium methoxide in methanol (10.9 ml). The mixture was stirred at 50° C. for 30 minutes, and under reduced pressure, the solvent was evaporated to give crystals, which were washed with water and dried to give (−)-7-(2-chlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (38.9 g). (This compound was confirmed to be S-isomer (absolute configuration), according to X-ray crystal structure analysis.)

Workup

  1. waitat room temperature for 2 days
  2. filtrationThe crystals were filtered
  3. washwashed with isopropylalcohol

Sources & evidence

ORD record
ord-d50298a45981484ebeff27a766832d62
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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