Methyl iodide → HCID 15092375, compound

HRID 1504842Notes

Reaction equation

HRID 1504842 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([C:22]([OH:24])=[O:23])[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](=O)([O-])[O-].[K+].[K+].CI>CS(C)=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([C:22]([O:24][CH3:25])=[O:23])[NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2755950Boc-dap(Z)-OH

Product 1

HCID 15092375HCID 15092375, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine (100 g, 0.29 mol), potassium carbonate (82 g, 0.59 mol) and methyl iodide (42 g, 0.29 mol) in DMSO (1200 mL) was stirred at room temperature. After 12 hours, the reaction mixture was extracted with ethyl acetate, and the organics were separated and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to give methyl 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alaninate. MS ESI calc'd. for C17H25N2O6 [M+H]+ 353. found 353. 1H NMR (400 MHz, CDCl3) δ 7.36-7.33 (m, 5H), 5.09 (s, 2H), 4.34-4.30 (m, 1H), 3.74 (s, 2H), 3.59 (t, J=6.0 Hz, 2H), 2.62 (s, 3H), 1.44 (s, 9H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customthe organics were separated
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a645d5363d924632882a740fa7a93c2f
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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