1-(Trimethylsilyl)ethanol → HCID 56636303, compound

HRID 1462497Notes

Reaction equation

HRID 1462497 reaction equation
[C:1]1(=[O:30])[N:5]([CH:6]2[CH2:11][S:10][C@H:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:7]2=[O:24])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12.[CH3:31][Si:32](C(O)C)([CH3:34])[CH3:33]>CCOCC.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:4]1(=[O:25])[N:5]([CH:6]2[CH2:11][S:10][C@H:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:8]([CH2:18][C:19]([O:21][CH2:22][CH2:23][Si:32]([CH3:34])([CH3:33])[CH3:31])=[O:20])[C:7]2=[O:24])[C:1](=[O:30])[C:2]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:3]12

Participants

5

Reactant 2

HCID 124478981-(Trimethylsilyl)ethanolHCID 86739556HCID 86739556, compound

Product 1

HCID 56636303HCID 56636303, compound

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

(R)-Dihydro-5-phthalimido-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, ethyl ester is heated in trimethylsilylethanol in the presence of titanium (IV) ethoxide. Upon completion of the reaction, the reaction mixture is diluted with ether, washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, and brine, dried (MgSO4), and concentrated in vacuo. The residue is purified chromatographically on silica gel to yield (R)-dihydro-5-phthalimido-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, trimethylsilylethyl ester.

Workup

  1. customUpon completion of the reaction
  2. washwashed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified chromatographically on silica gel

Sources & evidence

ORD record
ord-f15c427eebcc4eeea2a512fce199c00a
Source dataset
uspto-grants-1984_07
Patent number
US04460579

Reaction notes

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