Dimethylformamide → HCID 86741478, compound
Reaction equation
C(OC(N[C@H:12]([C:17]([NH2:19])=[O:18])[C@H:13]([CH2:15]O)O)=O)C1C=CC=CC=1.[Cl:20][CH2:21][C:22]([N:24]=[C:25]=[O:26])=[O:23].CN(C=[O:31])C>>[Cl:20][CH2:21][C:22]([NH:24][C:25]([O:31][NH:19][C:17](=[O:18])[CH2:12][CH2:13][CH3:15])=[O:26])=[O:23]Participants
Conditions
- Temperature
- -10 °C
Procedure
A solution of 0.268 g (1 mM) of Nα-benzyloxycarbonyl-4-hydroxy-L-allothreoninamide in 5 mL DMF was cooled to -10° C. and 0.12 g (1 mM) chloroacetylisocyanate was added and the reaction was stirred at -10° C. for 1 hr to give (2S,3S)-2-benzyloxy-carboxamido-3-hydroxy-4-(N-chloroacetylcarbamoyloxy-butanamide. To the above reaction mixture, 0.148 g (1.25 mM) methanesulfonylchloride was added at -15° to -10° C. and 0.26 mL triethylamine was added subsequently. The reaction mixture was stirred at -15° to -10° C. for 40 min. After the reaction, ethylacetate (20 mL) was added. The resulting mixture was washed with 5% aqueous NaH2PO4, brine and the organic layer was dried over Na2SO4. Solvent was removed at the reduced pressure and the crude product was purified by column chromatograph (SiO2, EtOAc:Hexane-8:2) to give (2S, 3S)-2-benzyloxycarboxamido-3-methanesulfonyloxy-4-(N-chloroacetylcarbamoyloxy)-butanamide 0.25 g (53%).
Sources & evidence
- ORD record
- ord-32c839a1af2745d8bde0690e5056def3
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04663469
Reaction notes
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