Hydrochloric Acid → HCID 25258315, compound

HRID 422903Notes

Reaction equation

HRID 422903 reaction equation
[SH:1][CH2:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)[C:4]([OH:6])=[O:5].Cl>CC(O)(C)C>[C:3]([S:1][CH2:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)[C:4]([OH:6])=[O:5])([CH3:7])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25258314HCID 25258314, compound

Product 1

HCID 25258315HCID 25258315, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To the reaction mixture of step 5, under N2 atmosphere, was injected a mixture of t-BuOH (3 ml) and 37% HCl (2.5 ml). The reaction mixture was heated to reflux for 4 hours, then cooled to room temperature and partitioned between water and CH2Cl2. The combined CH2Cl2 phases were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with 0 to 5% EtOH in CH2Cl2 to give 2-(S-t-butylsulfanylmethyl)-3-(3-bromophenyl)propionic acid as a colorless, viscous oil, 0.133 g, 51%: HPLC purity: 94.5%, MS (ES−) [M−H+]: 329, 331.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. custompartitioned between water and CH2Cl2
  4. washThe combined CH2Cl2 phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 0 to 5% EtOH in CH2Cl2

Sources & evidence

ORD record
ord-9c644f585f394612ab8ab8666f5e97e6
Source dataset
uspto-grants-2012_01
Patent number
US08101665B2

Reaction notes

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