Chlorotrimethylsilane → Methyl L-ornithine dihydrochloride

HRID 2250314Notes

Reaction equation

HRID 2250314 reaction equation
C(OC([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][CH2:12][NH2:13])=O)(C)(C)C.[CH:17](C1C=CC=CC=1B(O)O)=O.[BH4-].[Na+].C[Si]([Cl:34])(C)C>CO.C(N(CC)CC)C.CO>[ClH:34].[ClH:34].[NH2:8][C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:11][CH2:12][NH2:13]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 2921892-Formylphenylboronic acidHCID 4311764Sodium borohydrideHCID 7018784(2S)-5-amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Product 1

HCID 14273060Methyl L-ornithine dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22728368Triethylamine methanolSolvent

Procedure

Nα-tert-Butyloxycarbonyl-ornitine 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 treatment with methanol and trimethylsilyl chloride, 10:1, to give N′-(2-boronobenzyl), methyl ornitinate, dihydrochloride.

Sources & evidence

ORD record
ord-e5be11ac50d145e5aeab1635078a5117
Source dataset
uspto-grants-2008_01
Patent number
US07316999B2

Reaction notes

Loading…