Trifluoroacetic acid methylene chloride → (2S,3R)-2-amino-3-azido-butyric acid methylester hydrochloride
Reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([NH:10]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C@H:5]([N:7]=[N+:8]=[N-:9])[CH3:6].C(O)(C(F)(F)F)=O.C(Cl)[Cl:39]>Cl>[ClH:39].[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([NH2:10])[C@H:5]([N:7]=[N+:8]=[N-:9])[CH3:6]Participants
4
Procedure
A solution of Trt-Azido-Thr-OMe (3) (4.8 g, 12.0 mmol) was dissolved in a 95% TFA/DCM solution (60 ml) at rt with stirring. After 2.5 h, the reaction was complete by LCMS. The bright yellow solution was diluted with 0.5 N aq. HCl (300 ml). The aqueous layer was extracted with DCM (2×30 ml) and then lyophilized to dryness. The white solid was dissolved in AcCN/water (50:50) (100 ml) and again lyophilized to dryness to produce a consistent powder and remove as much of the TFA as possible. The azido-Thr product (4), 2.26 g (97% yield, 95% pure) of a white solid, was obtained as the HCl salt.
Workup
- extractionThe aqueous layer was extracted with DCM (2×30 ml)
- dissolutionThe white solid was dissolved in AcCN/water (50:50) (100 ml)
- customto produce a consistent powder
- customremove as much of the TFA as possible
Sources & evidence
- ORD record
- ord-1e0ec3529539430c81a0cbaaa63930b8
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153843B2
Reaction notes
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