Trimethylsilyldiazomethane → 687-64-9

HRID 2250312Notes

Reaction equation

HRID 2250312 reaction equation
C(OC([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(C)C)=O)(C)(C)C.[CH3:21][Si](C=[N+]=[N-])(C)C>C(O)C.CCOCC>[NH2:8][C@H:9]([C:18]([O:20][CH3:21])=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 14840637N-α-Boc-N-ε-isopropyl-L-lysine

Product 1

HCID 117779687-64-9

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Nα-tert-Butyloxycarbonyl-Nε-isopropyl lysine (SennChem) was reacted with trimethylsilyldiazomethan in ethanol. The resulting methyl ester amine was reacted with 2-(pinacolborono)benzyl bromide in ether and TEA to give Nα-tert-butyloxycarbonyl, Nε-isopropyl, Nε-(2-pinacolboronobenzyl) methyl lysinate:

Sources & evidence

ORD record
ord-d18d5090e9694c9ea122abb2c69fbee2
Source dataset
uspto-grants-2008_01
Patent number
US07316999B2

Reaction notes

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