(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid → (2S)-5-amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid
Reaction equation
[NH:1]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][CH2:5][NH:6]C(OCC1C=CC=CC=1)=O>CO.[H][H]>[NH:1]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][CH2:5][NH2:6]Participants
4
Procedure
Boc-Orn-OH (0.51 g) [obtained by catalytically reducing Boc-Orn(Z)-OH in methanol in a stream of hydrogen using 10% Pd-carbon as a catalyst] was dissolved in DMF, and the solution was cooled with ice. TEA (0.61 ml) and PhCOONB [prepared from PhCOOH (0.30 g), HONB (0.47 g) and DCC (0.54 g)] were added thereto, followed by stirring overnight. The reaction solution was concentrated, and the residue was dissolved in AcOEt. The resulting solution was washed with 10% aqueous citric acid. After washing with water, the solution was dried with Na2SO4 and concentrated. Then, ether and dicyclohexylamine (438 μl) were added to the residue to separate out a precipitate, which was collected by filtration.
Sources & evidence
- ORD record
- ord-76f61e910fc64ed8a2c2929b9d4b83e9
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616684
Reaction notes
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