Lithium Hydroxide → HCID 59923474, compound

HRID 2297712Notes

Reaction equation

HRID 2297712 reaction equation
[SH:1][CH2:2][CH2:3][N:4]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5](=[O:13])[NH:6][C@H:7]1[CH2:12][CH2:11][O:10][C:8]1=[O:9].[OH-:22].[Li+]>CO>[OH:10][CH2:11][CH2:12][C@H:7]([NH:6][C:5]([N:4]([CH2:3][CH2:2][SH:1])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:8]([OH:22])=[O:9]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18337258HCID 18337258, compound

Product 1

HCID 59923474HCID 59923474, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S)-2-[3-(2-Mercaptoethyl)-3-phenethylureido]-4-butanolide (Compound No. 1-69, 2.9 g) is dissolved in methanol (19 ml) under a nitrogen atmosphere. A 2 N aqueous lithium hydroxide solution (5.6 ml) is added thereto under ice cooling, and the mixture is stirred under ice cooling for 50 minutes and further at room temperature for 35 minutes. The reaction mixture is concentrated under reduced pressure, a 10% aqueous citric acid solution is added to the concentrate, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.5 g (48%) of the titled compound (Compound No. 8-1).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additiona 10% aqueous citric acid solution is added to the concentrate
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe organic layer is washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d1906394d02744a29d71c3c5c4e5a2c1
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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