Benzyl (3-chloro-3-oxopropyl)carbamate → HCID 45082345, compound

HRID 1698875Notes

Reaction equation

HRID 1698875 reaction equation
[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]

Participants

3

Reactant 2

HCID 13375984Benzyl (3-chloro-3-oxopropyl)carbamateHCID 178501479HCID 178501479, compound

Product 1

HCID 45082345HCID 45082345, compound

Procedure

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.

Sources & evidence

ORD record
ord-dd15f6fdec0b4ce8bf43104a5e76be03
Source dataset
uspto-grants-2002_02
Patent number
US06344483B1

Reaction notes

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