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

HRID 1737940Notes

Reaction equation

HRID 1737940 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[C:5](=[O:26])[CH:6]([NH:13][C:14](=[O:25])[C:15](=[C:20]1[S:24][CH:23]=[CH:22][S:21]1)[C:16]([O:18]C)=[O:17])[CH2:7][CH2:8][C:9]([O:11]C)=[O:10])[CH2:2][CH3:3].[OH-].[K+]>CO>[C:16]([C:15](=[C:20]1[S:21][CH:22]=[CH:23][S:24]1)[C:14]([NH:13][CH:6]([C:5]([N:4]([CH2:27][CH2:28][CH3:29])[CH2:1][CH2:2][CH3:3])=[O:26])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:25])([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15432127Methyl 5-(dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)-3-methoxy-3-oxopropanoyl)amino)-5-oxopentanoate

Product 1

HCID 154321284-((2-Carboxy-2-(1,3-dithiol-2-ylidene)acetyl)amino)-5-(dipropylamino)-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-(dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)-3-methoxy-3-oxopropanoyl)amino)-5-oxopentanoate (5) (111 g) was dissolved in methanol (1 l), followed by the addition of 2.5 N potassium hydroxide solution (300 ml). The resulting mixture was heated under reflux for 2 hours. The solvent was removed under reduced pressure. The resulting residue was washed several times with water, whereby 4-((2-carboxy-2-(1,3-dithiol-2-ylidene)acetyl)amino)-5-(dipropylamino)-5-oxopentanoic acid (6) was obtained as a waxy substance. Without purification, the reaction product was provided for use in the next example.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. washThe resulting residue was washed several times with water

Sources & evidence

ORD record
ord-498b1fea42174e4b90db5c8457e451b2
Source dataset
uspto-grants-1999_10
Patent number
US05962509

Reaction notes

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