Triethylamine → HCID 131719289, compound

HRID 1440070Notes

Reaction equation

HRID 1440070 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH3:10])[C:7](Cl)=[O:8])(=[O:3])[CH3:2].Cl.[NH2:12][C@H:13]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:15][S:16][CH3:17].C(N(CC)CC)C>C(Cl)Cl>[C:1]([S:4][CH2:5][CH:6]([CH3:10])[C:7]([NH:12][C@H:13]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:15][S:16][CH3:17])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 131719289HCID 131719289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Acetylthio-2-methylpropanoyl chloride (3.78 ml., 25 mmole) is added dropwise over six minutes to a cold (-5°), stirred suspension of (L)-methionine, methyl ester, hydrochloride salt (4.99, 25 mmole) and triethylamine (13.94 g.) in methylene chloride (100 ml.). The mixture is stirred in the cold for three hours and then diluted with methylene chloride (100 ml.). The resulting yellow solution is washed sequentially with 10% aqueous HCl (70 ml.), saturated sodium bicarbonate (70 ml.) and brine (100 ml.), dried over sodium sulfate, and concentrated in vacuo to give (±)-N-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-methionine, methyl ester.

Workup

  1. stirringThe mixture is stirred in the cold for three hours
  2. washThe resulting yellow solution is washed sequentially with 10% aqueous HCl (70 ml.), saturated sodium bicarbonate (70 ml.) and brine (100 ml.)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50cb59c6a5324320a57086abeea0d684
Source dataset
uspto-grants-1996_03
Patent number
US05496805

Reaction notes

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