4-Methylmorpholine → tert-butyl((R)-1-furan-3-ylmethyl-2-hydroxy-ethyl)-carboxylate
Reaction equation
N[C@H:2]([CH2:6][C:7]1[CH:11]=[CH:10][O:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(OC(N[C@H]([CH2:24][C:25]1[CH:29]=CO[CH:26]=1)C(O)=O)=O)(C)(C)C.CN1CC[O:34][CH2:33]C1.C(OC(Cl)=O)C(C)C>C(COC)OC>[O:9]1[CH:10]=[CH:11][C:7]([CH2:6][C@@H:2]([C:3]([O:5][C:25]([CH3:29])([CH3:26])[CH3:24])=[O:4])[CH2:33][OH:34])=[CH:8]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
Starting from (R)-2-amino-3-furan-3-yl-propionic acid (DE3829451), (R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid is prepared. Under argon 420 mg (R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid are suspended in 2.5 ml dimethoxyethane suspended. The reaction mixture is cooled to −30° C. 220 μl N-methylmorpholine are added and then 240 μl isobutylchloroformate in 1.5 ml dimethoxyethane is added dropwise. The reaction mixture is allowed to come up to −5° C. and the precipitate is quickly filtered. The filtrate is cooled to −15° C. 100 mg sodium borohydride and a few drops of water are added. The reaction mixture is stirred for 1 hour at ambient temperature and evaporated to dryness. The residue is suspended in ethyl acetate. The reaction mixture is dried and evaporated to dryness. 370 mg of the product are obtained as a solid. Analytical HPLC-MS (method D): RT=1.21 min.
Workup
- customis prepared
- customto come up to −5° C.
- filtrationthe precipitate is quickly filtered
- temperatureThe filtrate is cooled to −15° C
- addition100 mg sodium borohydride and a few drops of water are added
- customevaporated to dryness
- customThe reaction mixture is dried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-9783a9c1ea584defa38d1e4af59bb47e
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822474B2
Reaction notes
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