Chlorotrimethylsilane → HCID 18753514, compound

HRID 1838419Notes

Reaction equation

HRID 1838419 reaction equation
[CH3:1][Si](Cl)(C)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18]([CH2:22][CH2:23][N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[C:19]([OH:21])=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1>CO.O1CCCC1>[CH3:1][O:20][C:19](=[O:21])[CH:18]([CH2:22][CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])[NH:17][S:14]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=1)(=[O:15])=[O:16]

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 9931820HCID 9931820, compound

Product 1

HCID 18753514HCID 18753514, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

After addition of trimethylsilyl chloride (0.65 g, 5.1 mmol) to a solution of (±)-N-(4-methoxybenzensulfonyl)-2-(2-phthalimidoethyl)glycine (1.08 g, 2.6 mmol), the product of Example 21, in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml), the mixture was heated under reflux for 2 hours. The solvent of the reaction mixture was evaporated under reduced pressure. To the residue, a saturated aqueous solution of sodium hydrogencarbonate was added and this was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hexane was added to the residue for caking to afford the desired compound (yield 96%) as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent of the reaction mixture was evaporated under reduced pressure
  4. additionTo the residue, a saturated aqueous solution of sodium hydrogencarbonate was added
  5. extractionthis was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionHexane was added to the residue

Sources & evidence

ORD record
ord-94ce449238d84abc9d41acddbb94492c
Source dataset
uspto-grants-2004_01
Patent number
US06673804B1

Reaction notes

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