Triethylamine → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

HRID 449483Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH2:29][C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1)[C:25]([O:27][CH3:28])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:28][O:27][C:25](=[O:26])[C@@H:24]([NH:23][C:21]([O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:22])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Trifluoromethanesulfonic anhydride (0.85 mL, 5.1 mmol) was added to a solution of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate (1 g, 3 mmol) (Aldrich, Cat 469106) and triethylamine (1 mL, 10 mmol) in methylene chloride (30 mL) at −78° C. The reaction was stirred for 1 h. at −78° C. Saturated NaHCO3 was added and the reaction was extracted with dichloromethane. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) to obtain (S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxy-phenyl)-propionic acid methyl ester (1.2 g, 80%) as light yellow oil. Analytical LCMS (M+H-Boc)+: m/z=327.9.

Workup

extractionthe reaction was extracted with dichloromethane
washThe organic phase was washed with saturated brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)

Sources & evidence

ORD record: ord-7a017bcc06d24e959627b176b1f0afd7
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481732B2

Reaction notes

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