Triethylamine → N-(3-acetylthio-2-methylpropanoyl)-N-(3-methylthiopropyl)glycine t-butyl ester

HRID 127619Notes

Reaction equation

HRID 127619 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][S:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:22]([S:25][CH2:26][CH:27]([CH3:31])[C:28](Cl)=[O:29])(=[O:24])[CH3:23]>O1CCOCC1>[C:1]([O:5][C:6](=[O:14])[CH2:7][N:8]([C:28](=[O:29])[CH:27]([CH3:31])[CH2:26][S:25][C:22](=[O:24])[CH3:23])[CH2:9][CH2:10][CH2:11][S:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 20285453N-(3-methylthiopropyl)glycine t-butyl ester

Product 1

HCID 20285472N-(3-acetylthio-2-methylpropanoyl)-N-(3-methylthiopropyl)glycine t-butyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(3-methylthiopropyl)glycine t-butyl ester (36.4 g, 0.166 mol) and triethylamine (20.2 g, 0.199 mol) in 300 ml of dioxane was added dropwise 3-acetylthio -2-methylpropanoyl chloride (30.0 g, 0.166 mol). After stirring at room temperature for 16 hours the mixture was filtered and concentrated to yield 52.9 g. Purification by medium pressure liquid chromatography eluting with 20% ethyl acetate in hexane gave 18.0 g (30%) of N-(3-acetylthio-2-methylpropanoyl)-N-(3-methylthiopropyl)glycine t-butyl ester as a colorless oil. Rf =0.19 (20% ethyl acetate in hexane).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. customto yield 52.9 g
  4. customPurification by medium pressure liquid chromatography
  5. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7816cd3db9204078b4b3eb13690da60d
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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