Pyridine → 3-Amino-2-{[(tert-butoxy)carbonyl]amino}propanoic acid
Reaction equation
C[N:2](C)C=O.FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.[CH3:27][C:28]([O:31][C:32]([NH:34][C@@H:35]([C:40]([OH:42])=[O:41])[CH2:36]C(N)=O)=[O:33])([CH3:30])[CH3:29].N1C=CC=CC=1>O>[CH3:30][C:28]([O:31][C:32]([NH:34][CH:35]([C:40]([OH:42])=[O:41])[CH2:36][NH2:2])=[O:33])([CH3:27])[CH3:29]Participants
6
Procedure
To a 1:1 dimethylformamide:water solution (170 ml) of [bis(trifluoroacetoxy)iodo]benzene (12.89 g, 32.29 mmol, 1.5 equiv) was added N-α-BOC-D-asparagine (5 g, 21.53 mmol, 1 equiv). This solution stirred at room temperature for 0.5 h before pyridine (3.4 g, 43.06 mmol, 2 equiv) was added. After 18 h the reaction was concentrated in vacuo and the residue was redissolved in water before being washed with diethyl ether (2×, 50 ml). The aqueous layer was concentrated in vacuo and the crude product was recrystallized from hot acetonitrile to give E7-1 (1.10 g, 25% yield).
Workup
- additionwas added
- concentrationAfter 18 h the reaction was concentrated in vacuo
- dissolutionthe residue was redissolved in water
- washbefore being washed with diethyl ether (2×, 50 ml)
- concentrationThe aqueous layer was concentrated in vacuo
- customthe crude product was recrystallized from hot acetonitrile
- customto give E7-1 (1.10 g, 25% yield)
Sources & evidence
- ORD record
- ord-1ea533faa16949baaef758d53a6a74d3
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06653281B1
Reaction notes
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