Water → HCID 13472321, compound

HRID 1248056Notes

Reaction equation

HRID 1248056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([NH:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:8][CH2:7][CH2:6]2.[C:18]([S:21][CH2:22][CH:23]([CH3:27])[C:24](Cl)=[O:25])(=[O:20])[CH3:19].O>CC(N(C)C)=O>[C:18]([S:21][CH2:22][CH:23]([CH3:27])[C:24]([N:13]([CH:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1)[CH2:14][C:15]([OH:17])=[O:16])=[O:25])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 12851971HCID 12851971, compound

Product 1

HCID 13472321HCID 13472321, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(6-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)glycine (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 20 ml of 10% hydrochloric acid and with water, and dried over anhydrous sodium sulfate. Ethyl acetate is distilled off under reduced pressure, 10 ml of ethyl ether is added to the residue, and the mixture is allowed to stand at room temperature. Collection of the resulting crystalline precipitate by filtration gives 1.9 g of N-(3-acetylthio-2-methylpropionyl)-N-(6-methoxy-1,2,3,4-tetrahydro-1-naphthyl)glycine as colorless needles. Melting point: 158°-161° C.

Workup

  1. stirringstirring
  2. extractionextracted with 200 ml of ethyl acetate
  3. washThe extract is washed with 20 ml of 10% hydrochloric acid and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationEthyl acetate is distilled off under reduced pressure, 10 ml of ethyl ether
  6. additionis added to the residue
  7. customto stand at room temperature
  8. customCollection of the resulting crystalline precipitate
  9. filtrationby filtration

Sources & evidence

ORD record
ord-0d8eb4a58c2146919cd5d38142c7907d
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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