Acetone → HCID 23135943, compound

HRID 2377564Notes

Reaction equation

HRID 2377564 reaction equation
[CH3:1][C@@:2]([C:6]([OH:8])=[O:7])([CH2:4][SH:5])[NH2:3].[CH3:9][C:10]([CH3:12])=O>CO>[CH3:9][C:10]1([CH3:12])[NH:3][C:2]([CH3:1])([C:6]([OH:8])=[O:7])[CH2:4][S:5]1

Participants

4

Conditions

Temperature
56 °C

Procedure

2.00 g of 2,2,4-trimethylthiazolidine-4-carboxamide hydrochloride prepared by the method described in Justus Liebigs Ann. Chem. (1966), 697, 140-157, was dissolved in 10 ml of 36% concentrated hydrochloric acid. The obtained solution was then heated to reflux at 105° C. for 1 hour, followed by concentration and drying. The thus obtained white solid was washed with isopropanol to obtain 1.62 g of 2-methylcysteine hydrochloride. This compound was converted into an aqueous solution, and the solution was passed through an anion exchange resin for desalinization. Thereafter, it was evaporated to dryness to obtain 1.27 g of 2-methylcysteine. The total amount of the obtained 2-methylcysteine was dissolved in 5 ml of methanol, and thereafter, 5 ml of acetone was added thereto, followed by heating to reflux at 56° C. Four hours later, the heating was terminated, and the reaction solution was concentrated and dried. The obtained white solid was then washed with acetone to obtain 1.32 g of 2,2,4-trimethylthiazolidine-4-carboxylic acid. The yield was found to be 80 mol % relative to the 2-methylcysteine hydrochloride as the raw material. The obtained 2,2,4-trimethylthiazolidine-4-carboxylic acid had the following physical properties:

Workup

  1. temperatureby heating
  2. customFour hours later, the heating was terminated
  3. concentrationthe reaction solution was concentrated
  4. customdried
  5. washThe obtained white solid was then washed with acetone

Sources & evidence

ORD record
ord-622c5cc7c36242b38cd9877ba7d22db2
Source dataset
uspto-grants-2008_12
Patent number
US07470525B2

Reaction notes

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