Methanol → 3417-91-2

HRID 1775748Notes

Reaction equation

S(Cl)([Cl:3])=O.[NH2:5][C@H:6]([C:15]([OH:17])=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[CH3:18]O>>[Cl-:3].[OH:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C@H:6]([NH3+:5])[C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 887Methanol

HCID 6057L-Tyrosine

HCID 24386Thionyl Chloride

Product 1

HCID 110098083417-91-2Yield 84%

Procedure

Thionyl chloride (6.62 mmol, 0.48 mL) was added dropwise to a solution of L-tyrosine (0.600 g, 3.31 mmol) in methanol (22 mL). The reaction was heated to reflux with vigorous stirring for 24 h. After cooling, the reaction mixture was concentrated under reduced pressure and the residual methanol removed by azeotropic distillation with dichloromethane (10 mL) under reduced pressure to give the title compound as a white solid (0.646 g, 84%).

Workup

temperatureThe reaction was heated
temperatureto reflux
temperatureAfter cooling
concentrationthe reaction mixture was concentrated under reduced pressure
customthe residual methanol removed by azeotropic distillation with dichloromethane (10 mL) under reduced pressure

Sources & evidence

ORD record: ord-89e1efe539f040d8b8fd5837c3c7eb64
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260460B2

Reaction notes

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