Methyl iodide → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-cyanopropanoate

HRID 1171962Notes

Reaction equation

HRID 1171962 reaction equation
IC.[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][C:16]#[N:17])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:18]1CCN2C(=NCCC2)CC1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:18][O:13][C:12](=[O:14])[C@@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:15][C:16]#[N:17]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516920Potassium bisulfateHCID 7019873Boc-beta-cyano-L-alanine

Product 1

HCID 76850178(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-cyanopropanoateYield 86.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (2.18 ml, 35.01 mmol) was added to a mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (5.00 g, 23.34 mmol) and DBU (3.67 ml, 24.51 mmol) in toluene (20 mL) at rt. The reaction was stirred at 50 C for 2 days. Water (20 mL), saturated KHSO4 (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (hexane:Ethyl acetate=2:1) to give the (S)-methyl-2-(tert-butoxycarbonylamino)-3-cyanopropanoate as white solid (4.6 g, 86%). 1H NMR (400 MHz, d6-DMSO) δ7.64 (d, J=8.8 Hz, 1H), 4.39 (m, 1H), 3.66 (s, 3H), 2.96 (dd, J=16.8 Hz & 5.1 Hz, 1H), 2.85 (dd, J=16.8 Hz & 5.2 Hz, 1H), 1.40 (s, 9H).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by chromatography (hexane:Ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a49283446fa94e4398bd2209b4db3a85
Source dataset
uspto-grants-2010_11
Patent number
US07829665B2

Reaction notes

Loading…