Hydrochloric Acid → S-(4-Methylbenzyl)-L-Cysteine t-Butyl Ester

HRID 1651713Notes

Reaction equation

HRID 1651713 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[CH3:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][S:11][CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[CH:8][CH:7]=1.OS(O)(=O)=O.[OH-].[Na+].Cl>O1CCOCC1.CCOCC>[C:2]([O:17][C:15](=[O:16])[C@H:13]([CH2:12][S:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]([CH3:5])=[CH:19][CH:18]=1)[NH2:14])([CH3:3])([CH3:1])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 13994756S-p-Methylbenzyl-L-cysteine

Product 1

HCID 14770807S-(4-Methylbenzyl)-L-Cysteine t-Butyl Ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a cold solution of isobutylene (50 ml) in dioxane (80 ml), add S-(4-methylbenzyl)-L-cysteine (5.0 g) and concentrated H2SO4 (10 ml). Seal the vessel, allow to warm to room temperature, and stir for 18 hr. Pour into 5% NaOH (500 ml), extract with Et2O (3×400 ml), dry (MgSO4) and concentrate the Et2O in vacuo to give an oil. Treat the oil with HCl in Et2O to give the title compound, white needles (2.76 g) m.p. 218° (dec).

Workup

  1. customSeal the vessel
  2. extractionextract with Et2O (3×400 ml)
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate the Et2O in vacuo
  5. customto give an oil

Sources & evidence

ORD record
ord-7b04dbd7580448f2be6f0002e56d6b62
Source dataset
uspto-grants-1990_05
Patent number
US04929641

Reaction notes

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