Benzyl (3-chloro-3-oxopropyl)carbamate → L-Lysine, 4-oxo-

HRID 1698875ノート

反応式

HRID 1698875 の反応式
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6]([O:8]C)=[O:7])[CH2:3][Zn]I.[NH:17](C(OCC1C=CC=CC=1)=O)[CH2:18][CH2:19][C:20](Cl)=[O:21]>>[O:21]=[C:20]([CH2:19][CH2:18][NH2:17])[CH2:3][C@@H:2]([C:6]([OH:8])=[O:7])[NH2:1]

参加物

3

反応物 2

HCID 13375984Benzyl (3-chloro-3-oxopropyl)carbamateHCID 178501479HCID 178501479、化合物

生成物 1

HCID 45082345L-Lysine, 4-oxo-

実験手順

Boc-L-Ala(ZnI)-OMe is reacted with Z-beta-Ala-Cl under conditions described in J. Org Chem 57, 1992, pp 3397-3404 to give a protected 4-keto-L-lysine which is then dissolved in DCM and treated with DAST to yield protected 4,4-difluoro-L-lysine. The epsilon carbobenzoxy protecting group is then removed under catalytic hydrogenolysis conditions. The resulting compound is reacted with methyl acetimidate hydrochloride to yield the epsilon amidine which was then reacted with 2 N HCl to give the title compound.

出典と根拠

ORDレコード
ord-dd15f6fdec0b4ce8bf43104a5e76be03
出典データセット
uspto-grants-2002_02
特許番号
US06344483B1

反応ノート

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