L-Pyroglutamic Acid → HCID 178428152, compound

HRID 1700731Notes

Reaction equation

HRID 1700731 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([Cl:7])[S: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>[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:6]=[C:5]([Cl:7])[S: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 178428150HCID 178428150, compound

Product 1

HCID 178428152HCID 178428152, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of (±)-7-(3,5-dichlorothiophen-2-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (1.6 g) in ethanol (10 ml) was added a solution of L-pyroglutamic acid (0.56 g) in ethanol (2 ml) at 80° C., and the mixture was gradually cooled to room temperature and stirred at room temperature for 6 hours. The resulting crystals were filtered and washed with ethanol to give (+)-7-(3,5-dichlorothiophen-2-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (1.2 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 (0.6 g). Under reduced pressure, the solvent was evaporated. The resulting crystals were washed with water, dried and dissolved in ethanol (10 ml). To the solution was added methanesulfonic acid (0.098 g), and the mixture was concentrated. The resulting crystals were recrystallized from ethanol to give (+)-7-(3,5-dichlorothiophen-2-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound 143) (0.1 g,99.6%ee).

Workup

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

Sources & evidence

ORD record
ord-c44dbe24ec584bd9b6f568bddc2c51c1
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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