L-(+)-Cysteine → HCID 18667310, compound

HRID 1456958Notes

Reaction equation

HRID 1456958 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[C:8]([C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[CH:15]=O)([CH3:11])([CH3:10])[CH3:9]>CO>[C:21]([C:18]1[CH:17]=[C:14]([CH:15]2[NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]2)[CH:13]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:19]=1[OH:20])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 5862L-(+)-CysteineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 18667310HCID 18667310, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of cysteine (Aldrich, 2.0 g, 17.1 mmol) and 3,5-di-tert-butyl-4-hydroxybenzaldehyde (Aldrich, 4.0 g, 17.1 mmol) in methanol (100 mL) was warmed at reflux for 2.25 h. The reaction mixture was cooled to ambient temperature and the solid that formed upon cooling was collected by filtration. The solid was washed with methanol and recrystallized from a mixture of ethanol/ethyl acetate. Recrystallization from ethanol gave 1.3 g (22% yield) of (4R)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-thiazolidine carboxylic acid as an off white solid, m.p. 163°-165° C.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 2.25 h
  3. customthe solid that formed
  4. temperatureupon cooling
  5. filtrationwas collected by filtration
  6. washThe solid was washed with methanol
  7. customrecrystallized from a mixture of ethanol/ethyl acetate
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-1efa4e565ca747799d14af69a154b5c7
Source dataset
uspto-grants-1998_12
Patent number
US05846988

Reaction notes

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