L-(-)-Ornithine → Fmoc-Orn(Fmoc)-OH

Reaction equation

Cl[C:2]([O:4][CH2:5][CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3].[NH2:19][C@H:20]([C:25]([OH:27])=[O:26])[CH2:21][CH2:22][CH2:23][NH2:24]>>[CH:17]1[C:18]2[CH:6]([CH2:5][O:4][C:2]([NH:19][C@H:20]([C:25]([OH:27])=[O:26])[CH2:21][CH2:22][CH2:23][NH:24][C:2]([O:4][CH2:5][CH:6]3[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]4[C:18]3=[CH:17][CH:16]=[CH:15][CH:14]=4)=[O:3])=[O:3])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 6262L-(-)-Ornithine

HCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 13783707Fmoc-Orn(Fmoc)-OHYield 79%

Procedure

The reaction of 9-fluorenylmethyl chloroformate with L-ornithine according to the conditions described in example 2 provided the title product in 79% yield.

Sources & evidence

ORD record: ord-7a5fc84b0daf4aa8ae64d14cd3c3c3f8
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455587B1

Reaction notes

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