Methanol → 14907-27-8

HRID 1775747Notes

Reaction equation

S(Cl)([Cl:3])=O.[NH2:5][C@@H:6]([C:17]([OH:19])=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1.[CH3:20]O>>[Cl-:3].[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH2:7][C@@H:6]([NH3+:5])[C:17]([O:19][CH3:20])=[O:18])=[CH:9]1

Participants

Reactant 3

HCID 887Methanol

HCID 9060D-Tryptophan

HCID 24386Thionyl Chloride

Product 1

HCID 1118438714907-27-8Yield 86%

Procedure

Thionyl chloride (9.87 mmol, 0.72 mL) was added dropwise to a solution of D-tryptophan (1.000 g, 4.89 mmol) in methanol (33 mL). The reaction was heated to reflux with vigorous stirring for 24 h. After cooling, the reaction mixture was concentrated under reduced pressure and residual methanol traces removed by azeotropic distillation with dichloromethane (10 mL) under reduced pressure to give the title compound as a white solid (1.070 g, 86%).

Workup

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

Sources & evidence

ORD record: ord-eda62d7760f64825b27f69da4bebb08a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260460B2

Reaction notes

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