L-Pyroglutamic Acid → HCID 178428120, compound

HRID 1700729Notes

Reaction equation

HRID 1700729 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl: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]([Cl: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 178428118HCID 178428118, compound

Product 1

HCID 178428120HCID 178428120, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (±)-7-(2,5-dichlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (2.3 g) in ethanol (10 ml) was added a solution of L-pyroglutamic acid (0.81 g) in ethanol (5 ml) at 80° C., and the mixture was gradually cooled to room temperature and stirred for 6 hours. The resulting crystals were filtered and washed with ethanol to give (+)-7-(2,5-dichlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (1.61 g). Said crystals were recrystallized from ethanol and suspended in methanol, and to the suspension was added a solution of 28% sodium methoxide in methanol (0.5 g). Under reduced pressure, the solvent was evaporated. The resulting crystals were washed with water, dried, recrystallized from acetonitrile and dissolved in ethanol (10 ml). To the solution was added methanesulfonic acid (0.12 g), and the mixture was concentrated. The resulting crystals were recrystallized from ethanol to give (+)-7-(2,5-dichlorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound 141) (0.25 g,99.8%ee).

Workup

  1. filtrationThe resulting crystals were filtered
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-db69b7edf66848af965a87af4c547ada
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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