4-((2-Carboxy-2-(1,3-dithiol-2-ylidene)acetyl)amino)-5-(dipropylamino)-5-oxopentanoic acid → 5-(Dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)acetyl)amino)-5-oxopentanoic acid

HRID 1737941Notes

Reaction equation

C([C:4](=[C:23]1[S:27][CH:26]=[CH:25][S:24]1)[C:5]([NH:7][CH:8]([C:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[O:15])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:6])(O)=O>O1CCOCC1>[CH2:20]([N:16]([CH2:17][CH2:18][CH3:19])[C:14](=[O:15])[CH:8]([NH:7][C:5](=[O:6])[CH:4]=[C:23]1[S:27][CH:26]=[CH:25][S:24]1)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:21][CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

Dioxane (1.5 l) and activated carbon (10 g) were added to the 4-((2-carboxy-2-(1,3-dithiol-2-ylidene)acetyl)amino)-5-(dipropylamino)-5-oxopentanoic acid (6) obtained in Synthesis Example 4. The resulting mixture was stirred at 50° C. for 30 minutes. The activated carbon was filtered off, and the solvent was removed from the filtrate under reduced pressure. Acetone was added to the thus-obtained residue. The resulting crystals were collected by filtration, washed with water, acetone and diethyl ether, and then dried at 60° C. for 8 hours under reduced pressure, whereby 5-(dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)acetyl)amino)-5-oxopentanoic acid (1) (67 g, yield: 72% (based on the compound (5)) was obtained as pale yellow crystals.

Workup

customobtained in Synthesis Example 4
filtrationThe activated carbon was filtered off
customthe solvent was removed from the filtrate under reduced pressure
additionAcetone was added to the thus-obtained residue
filtrationThe resulting crystals were collected by filtration
washwashed with water, acetone and diethyl ether
dry with materialdried at 60° C. for 8 hours under reduced pressure, whereby 5-(dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)acetyl)amino)-5-oxopentanoic acid (1) (67 g, yield: 72% (
customwas obtained as pale yellow crystals

Sources & evidence

ORD record: ord-7649d7a799ae4cda904ae371c812d520
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05962509

Reaction notes

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