Methanol → 2(S)-amino-3(R)-(4-iodophenyl)-butyric acid, methyl ester hydrochloride

HRID 1596604Notes

Reaction equation

HRID 1596604 reaction equation
[NH2:1][C@@H:2]([C@@H:6]([C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=1)[CH3:7])[C:3]([OH:5])=[O:4].S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[NH2:1][C@@H:2]([C@@H:6]([C:8]1[CH:9]=[CH:10][C:11]([I:14])=[CH:12][CH:13]=1)[CH3:7])[C:3]([O:5][CH3:19])=[O:4]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 542162412(S)-amino-3(R)-(4-iodophenyl)-butyric acid

Product 1

HCID 867574002(S)-amino-3(R)-(4-iodophenyl)-butyric acid, methyl ester hydrochlorideYield 82%

Procedure

To an ice cooled solution of 2(S)-amino-3(R)-(4-iodophenyl)-butyric acid (124 mg, 0.42 mmol) in methanol (0.5 mL) was added dropwise thionyl chloride (150 μL, 2.0 mmol). Methanol (1 mL) was added and the reaction mixture was heated to reflux for 2 hr. After cooling, the mixture was filtered and the filtrate concentrated by rotoevaporation to yield 2(S)-amino-3(R)-(4-iodophenyl)-butyric acid, methyl ester hydrochloride (116 mg, 82% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hr
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate concentrated by rotoevaporation

Sources & evidence

ORD record
ord-64c0aafae0dc4312a4fc7df6d0a34bf1
Source dataset
uspto-grants-2001_09
Patent number
US06291511B1

Reaction notes

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