Dimethyl Sulfate → HCID 11966594, compound

HRID 2090094Notes

Reaction equation

HRID 2090094 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:21](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:2])([CH3:5])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2734499N-(tert-Butoxycarbonyl)-4-chloro-L-phenylalanine

Product 1

HCID 11966594HCID 11966594, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 250 mL round bottom flask was added N-Boc-4-chloro-L-phenylalanine (0.971 g, 3.24 mmol), potassium carbonate (0.448 g, 3.24 mmol), a stir bar and 30 ml of acetone. To this was added dimethyl sulfate (0.613 ml, 6.48 mmol) and the reaction was allowed to proceed at ambient temperature for 36 h. The reaction was quenched with water (15 ml), and the product was extracted with ethyl acetate (4×100 ml). The organics were pooled, washed with brine, and dried over sodium sulfate. The organics were filtered and concentrated in vacuo to provide a pale yellow residue. The residue was purified by column chromatography on a Biotage SP1, 40M Biotage silica cartridge, eluting with a linear gradient of hexanes-ethyl acetate to provide the title compound as a pale yellow foam (950 mg). Mass spectrum (ESI) 214.1 (M-Boc). 1H NMR (600 MHz, CDCl3): δ 7.24 (d, J=8.3 Hz, 2H), 7.06 (d, J=8.1 Hz, 1H), 4.96 (d, J=7 Hz, 1H), 4.56 (d, J=6 Hz, 1H), 3.71 (s, 3H), 3.08 (dd, J=5.7, 5.7 Hz, 2H), 3.01 (dd, J=5.9, 6.0 Hz, 1H), 1.42 (s, 9H).

Workup

  1. customThe reaction was quenched with water (15 ml)
  2. extractionthe product was extracted with ethyl acetate (4×100 ml)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe organics were filtered
  6. concentrationconcentrated in vacuo
  7. customto provide a pale yellow residue
  8. customThe residue was purified by column chromatography on a Biotage SP1, 40M Biotage silica cartridge
  9. washeluting with a linear gradient of hexanes-ethyl acetate

Sources & evidence

ORD record
ord-23106bc833ab4d8b8ee869bb0707a9e4
Source dataset
uspto-grants-2013_05
Patent number
US08436028B2

Reaction notes

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