L-Pyroglutamic Acid → HCID 178428125, compound

HRID 1700655Notes

Reaction equation

[Cl:1][C:2]1[S:3][C:4]([Cl:23])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[N:18][NH:19][C:20]([NH2:22])=[NH:21])[CH2:8]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[S:3][C:4]([Cl:23])=[CH:5][C:6]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[N:18][NH:19][C:20]([NH2:22])=[NH:21])[CH2:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (±)-7-(2,5-dichlorothiophen-3-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (17.4 g) in ethanol (200 ml) was added a solution of L-pyroglutamic acid (4.0 g) in ethanol (20 ml), at 80° C., and the mixture was gradually cooled to the room temperature and stirred at room temperature for 6 hours. The crystals were filtered and washed with ethanol to give (+)-7-(2,5-dichlorothiophen-3-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (11.0 g). Said crystals were suspended in methanol (200 ml), and to the mixture was added a solution of 28% sodium methoxide in methanol (4.2 ml). Under reduced pressure, the solvent was evaporated to give crystals, which were washed with water, dried and recrystallized from ethanol. To the crystals was added ethanol (30 ml), and then methanesulfonic acid (3.4 g). The mixture was heated to give a homogenous solution and cooled, and precipitated crystals were filtered to give (+)-7-(2,5-dichlorothiophen-3-yl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound 111) (8.5 g, 99.9% ee).

Workup

filtrationThe crystals were filtered
washwashed with ethanol

Sources & evidence

ORD record: ord-686309dddf80420c915638554d4ca74a
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350749B1

Reaction notes

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