4-Methylmorpholine → L-(-)-Ornithine
Reaction equation
C([NH:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][CH2:11][CH2:12][NH:13]C(C(F)(F)F)=O)(OC(C)(C)C)=O.N[C@H](C(C(OC)=O)=O)CCCNC(C(F)(F)F)=O.CN1CCOCC1>>[NH2:8][C@H:9]([C:20]([OH:22])=[O:21])[CH2:10][CH2:11][CH2:12][NH2:13]Participants
4
Procedure
Bi-directional synthesis was then initiated by the coupling of acid 6 with amine 7 using isobutyl chloroformate for activation of 6 and NMM as a base, as shown in Scheme 2. This reaction proceeded smoothly to give the fully protected ornithine dimer 9 in 97% yield with sufficient purity after extractive work-up to be utilized directly in subsequent reactions. Ornithine dimer 9 was divided into two equal portions. The first part was hydrogenated giving 11 in quantitative yield, while the second part was treated with HCl giving the amine hydrochloride salt 10 in 83% yield. Both compounds were of sufficient purity after work-up to be utilized directly in the subsequent coupling.
Workup
- customBi-directional synthesis
Sources & evidence
- ORD record
- ord-e8b7bc840eff4f098951082cc11707d7
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067698B2
Reaction notes
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