Methanol → Penicillamine methyl ester

HRID 719667Notes

Reaction equation

HRID 719667 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].S(Cl)(Cl)=O.[CH3:14]O>>[NH2:1][C@@H:2]([C:3]([SH:6])([CH3:5])[CH3:4])[C:7]([O:9][CH3:14])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 92863L-Penicillamine

Product 1

HCID 153004Penicillamine methyl esterYield 100%

Procedure

To a methanol (18 mL, 1.14 M) solution containing L-penicillamine (3.0 g, 20.11 mmol, 1.0 eq) was added thionyl chloride (1.5 mL, 20.7 mmol, 1.03 eq). The resulting mixture was heated to reflux for 18 hr and the solvent removed in vacuo. The resulting clear semi-solid was used in the next step without further purification. Isolated 3.28 g (20.1 mmol, 100% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 18 hr
  3. customthe solvent removed in vacuo
  4. customThe resulting clear semi-solid was used in the next step without further purification
  5. customIsolated 3.28 g (20.1 mmol, 100% yield)

Sources & evidence

ORD record
ord-bd5e1b8e45af41ca92ca3e05f5afe5be
Source dataset
uspto-grants-2006_11
Patent number
US07132443B2

Reaction notes

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