Chlorotrimethylsilane → Methyl L-lysinate dihydrochloride

HRID 2250315Notes

Reaction equation

HRID 2250315 reaction equation
C(OC([NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=O)(C)(C)C.[CH:18](C1C=CC=CC=1B(O)O)=O.[BH4-].[Na+].C[Si]([Cl:35])(C)C>CO.C(N(CC)CC)C.CO>[ClH:35].[ClH:35].[NH2:8][C@H:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 2921892-Formylphenylboronic acidHCID 2733284epsilon-tert-Butyloxycarbonyl-lysineHCID 4311764Sodium borohydride

Product 1

HCID 117778Methyl L-lysinate dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22728368Triethylamine methanolSolvent

Procedure

Nα-tert-Butyloxycarbonyl-lysine was reacted with 2-formylphenylboronic acid in methanol-triethylamine and subsequently treated with sodium borohydride (Wiskur et al, Org. Letters 2001, 3, 1311). The resulting secondary amine was transformed to the methyl ester by treament with methanol and trimethylsilyl chloride, 10:1, to give Nε-(2-boronobenzyl), methyl lysinate, dihydrochloride.

Sources & evidence

ORD record
ord-c3dfc82ad86c44eea84e45ada6332616
Source dataset
uspto-grants-2008_01
Patent number
US07316999B2

Reaction notes

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