Water → Thioacetic acid S-((S)-2-tert-butoxycarbonylamino-4-methyl-pentyl)ester

HRID 1750183Notes

Reaction equation

HRID 1750183 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:10]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([O-:29])(=[S:28])[CH3:27].[K+].O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:10][S:28][C:26](=[O:29])[CH3:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14081313toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-methyl-pentyl esterHCID 23670855Potassium ethanethioate

Product 1

HCID 14186507Thioacetic acid S-((S)-2-tert-butoxycarbonylamino-4-methyl-pentyl)esterYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.00 g of toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-4-methyl-pentyl ester in 10 ml DMF were added 308 mg of potassium thioacetate. After 24 h at room temperature, the reaction was poured unto water, the pH was then adjusted to 9 and the mixture was extracted with ethyl acetate twice. The combined organic phases were washed with brine until neutral, dried over sodium sulphate and concentrated in vacuo. 0.67 g (90%) of Thioacetic acid S—((S)-2-tert-butoxycarbonylamino-4-methyl-pentyl)ester were obtained.

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washThe combined organic phases were washed with brine until neutral,
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84e740c976254d55a9f91dade3e6d585
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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