Water → Methyl 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3,3-dimethyl-4-pentenoate

HRID 23176Notes

Reaction equation

HRID 23176 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18](=O)(O)[O-].[Na+].CI.O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:15])[C:10]([O:12][CH3:18])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 113685192-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid

Product 1

HCID 22592865Methyl 2-[[(1,1-dimethylethoxy)carbonyl]amino]-3,3-dimethyl-4-pentenoateYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2(R/S)-(tert-butoxycarbonyl)amino-3,3-dimethyl-4-pentenoic acid (3.6 g, 15 mmol) and anhydrous sodium bicarbonate (3.78 g, 45 mmol) in 25 mL of DMF was added methyl iodide (1.03 mL, 17 mmol) dropwise. The mixture was stirred for 27 hours at room temperature, and then poured into water (100 mL). The mixture was extracted with 2:1 ethyl acetate:hexane (3×50 mL), and the combined organic layers were washed with 5% aq. sodium thiosulfate solution, water, sat. aq. sodium bicarbonate, and finally with brine. The organic layer was dried over magnesium sulfate, and concentrated to provide methyl 2(R/S)-(tert-butoxycarbonyl)amino-3,3-dimethyl4-pentenoate (3.37 g, 87%) as a syrup which was used without further purification.

Workup

  1. extractionThe mixture was extracted with 2:1 ethyl acetate
  2. washhexane (3×50 mL), and the combined organic layers were washed with 5% aq. sodium thiosulfate solution, water, sat. aq. sodium bicarbonate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fdab976717304b478acc82a42a43bbb7
Source dataset
uspto-grants-2005_02
Patent number
US06849732B2

Reaction notes

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