Methyl iodide → HCID 86731703, compound

HRID 1504822Notes

Reaction equation

HRID 1504822 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][O:11][CH2:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](=O)([O-])[O-].[K+].[K+].IC>CS(C)=O.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][O:11][CH2:12][CH3:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15058451N-(tert-Butoxy(hydroxy)methylidene)-O-ethylserine

Product 1

HCID 86731703HCID 86731703, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of N-(tert-butoxycarbonyl)-O-ethylserine (5.3 g, 22 mmol) and potassium carbonate (6.3 g, 45 mmol) in DMSO (80 mL) was added iodomethane (6.5 g, 45 mmol) at room temperature. After 12 hours, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via chromatography on silica gel to afford methyl N-(tert-butoxycarbonyl)-O-ethylserinate. MS ESI calc'd. for C11H22NO5 [M+H]+ 248. found 248. 1H NMR (400 MHz, CDCl3) δ 5.36 (d, J=8.0 Hz, 1H), 4.42-4.39 (m, 1H), 3.84-3.81 (m, 1H), 2.75 (s, 3H), 3.64-3.60 (m, 1H), 3.49-3.45 (m, 2H), 1.45 (s, 9H), 1.15 (t, J=7.2 Hz, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via chromatography on silica gel

Sources & evidence

ORD record
ord-3eec4a3bbd9c4adf8bf5b3bb8a3b3669
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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