Benzaldehyde → Methyl L-lysinate dihydrochloride

HRID 2250313Notes

Reaction equation

HRID 2250313 reaction equation
C(OC(N[C@H](C(O)=O)CCCCN)=O)(C)(C)C.C[Si](C=[N+]=[N-])(C)C.C(=O)C1C=CC=CC=1.[BH4-].[Na+].C=O.[Na].[NH2:38][C@H:39]([C:45]([O:47][CH3:48])=[O:46])[CH2:40][CH2:41][CH2:42][CH2:43][NH2:44].C[Si]([Cl:53])(C)C>C(O)C.CO>[ClH:53].[ClH:53].[NH2:38][C@H:39]([C:45]([O:47][CH3:48])=[O:46])[CH2:40][CH2:41][CH2:42][CH2:43][NH2:44]

Participants

11

Reactant 8

HCID 240BenzaldehydeHCID 712FormaldehydeHCID 6397ChlorotrimethylsilaneHCID 117779687-64-9HCID 167693TrimethylsilyldiazomethaneHCID 2733284epsilon-tert-Butyloxycarbonyl-lysineHCID 4311764Sodium borohydrideHCID 5360545Sodium

Product 1

HCID 117778Methyl L-lysinate dihydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Nα-tert-Butyloxycarbonyl-lysine was reacted with trimethylsilyldiazomethan in ethanol. The resulting methyl ester amine was transformed to the Nε-methyl derivative via benzaldehyde and sodium borohydride, formaldehyde and sodium boronhydride and hydrogenolysis (Andruszkiewicz, J. Pol. Chem. 1988, 62, 257) followed by N-alkylation with 2-(pinacolborono)benzyl bromide. The resulting Nα-tert-butyloxycarbonyl, Nε-methyl, Nε-(2-pinacolboronobenzyl) methyl lysinate was treated with methanol and trimethylsilyl chloride, 10:1, to give Nε-methyl, Nε-(2-boronobenzyl), methyl lysinate, dihydrochloride:

Sources & evidence

ORD record
ord-e54f311abcd944dcab3e5f668b1209c7
Source dataset
uspto-grants-2008_01
Patent number
US07316999B2

Reaction notes

Loading…