2-(Trimethylsilyl)ethanol → HCID 56636303, compound

HRID 1462494Notes

Reaction equation

HRID 1462494 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)([CH3:36])[CH2:33]CO>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]([CH3:36])([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 180132-(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 (isomer A) (1.0 g., 2.36 mmole) is heated in 2-trimethylsilylethanol (5.58 g., 47.2 mmole) in the presence of titanium (IV) ethoxide (135 mg., 0.59 mmole). 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 eluting with hexane/ethyl acetate (3:1) to give (R)-dihydro-5-phthalimido-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, 2-(trimethylsilyl)ethyl 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 eluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-0be7e2a5d01545aa87f161e3c2b34595
Source dataset
uspto-grants-1984_07
Patent number
US04460579

Reaction notes

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