Methyl iodide → Boc-L-Lys(Z)-OMe

HRID 1625693Notes

Reaction equation

HRID 1625693 reaction equation
IC.[C:3]([O-])([O-])=O.[K+].[K+].[CH2:9]([O:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][C@H:24]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:25]([OH:27])=[O:26])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C>[CH2:9]([O:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][C@H:24]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:25]([O:27][CH3:3])=[O:26])=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2724765Boc-Lys(Z)-OH

Product 1

HCID 11132998Boc-L-Lys(Z)-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (2.0 mL), K2CO3 (5.60 g), (S)-6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoic acid (1) (NovaBiochem, A29340), and anhydrous DMF (20 mL) were combined and stirred at ambient temperature for 2 hours. The reaction mixture was subjected to an aqueous work-up, affording (S)-methyl 6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoate (TU3000-090) as clear oil. MS (ESI+): calcd. 417.20. found 417.20 (MNa+), calcd. 295.16. found 295.209((M-Boc)H+). H-NMR (400 MHz, CDCl3):1.372 (2H, m), 1.425 (9H, s), 1.515 (2H, m), 1.623 (1H, m), 1.785 (1H, br.s), 3.175(2H, m), 3.723 (3H, s), 4.284 (1H, m), 4.848 (1H, br.s), 5.084 (3H, overlapping br.s and s), 7.344 (5H, m). C-NMR (100 MHz, CDCl3): 22.340, 28.268, 29.307, 32.313, 40.569, 52.272, 53.099, 66.597, 79.897, 128.061, 128.100, 128.471, 136.519, 155.435, 156.426, 173.230.

Sources & evidence

ORD record
ord-602aadb693d2423dafe0d85ea5a4d79a
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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