Water → HCID 13472310, compound

HRID 1248057Notes

Reaction equation

HRID 1248057 reaction equation
[CH:1]1([NH:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:16]([S:19][CH2:20][CH:21]([CH3:25])[C:22](Cl)=[O:23])(=[O:18])[CH3:17].O>CC(N(C)C)=O>[C:16]([S:19][CH2:20][CH:21]([CH3:25])[C:22]([N:10]([CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[C@H:11]([C:13]([OH:15])=[O:14])[CH3:12])=[O:23])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 13472332HCID 13472332, compound

Product 1

HCID 13472310HCID 13472310, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(1-Indanyl)alanine (3.0 g) is suspended in 30 ml of dimethylacetamide, then 3.3 g of 3-acetylthio-2-methylpropionyl chloride is added dropwise with stirring at room temperature, and thereafter stirring is continued at room temperature for 2 hours. The reaction mixture is poured into 200 ml of water, and extracted with 200 ml of ethyl acetate. The extract is washed with 10 ml of 10% hydrochloric acid and with water, and dried. The ethyl acetate is distilled off under reduced pressure, and the residue is crystallized from an ethyl ether-petroleum ether mixture, to give 2.3 g of N-(3-acetylthio-2-methylpropionyl)-N-(1-indanyl)alanine, colorless needles having a melting point of 133°-137° C.

Workup

  1. stirringstirring
  2. extractionextracted with 200 ml of ethyl acetate
  3. washThe extract is washed with 10 ml of 10% hydrochloric acid and with water
  4. customdried
  5. distillationThe ethyl acetate is distilled off under reduced pressure
  6. customthe residue is crystallized from an ethyl ether-petroleum ether mixture

Sources & evidence

ORD record
ord-f01ab042c6734f6187ca9cd2afb86515
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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