Diethyl Ether → HCID 21302842, compound

HRID 1061676Notes

Reaction equation

HRID 1061676 reaction equation
C(N(C(C)C)CC)(C)C.[OH:10][CH:11]([CH3:27])[CH:12]([NH:17][CH2:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:13]([O:15][CH3:16])=[O:14].FC(F)(F)S(O[Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])(=O)=O.C(OCC)C>C(Cl)Cl>[Si:34]([O:10][CH:11]([CH3:27])[CH:12]([NH:17][CH2:18][C:19](=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:13]([O:15][CH3:16])=[O:14])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86759891HCID 86759891, compound

Product 1

HCID 21302842HCID 21302842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (3.1 ml) is added to a solution of methyl (2RS,3RS)-3-hydroxy-2-(2-oxo-2-phenylethyl)aminobutyrate (3.70 g, Reference compound No. 46-10) in methylene chloride (35 ml). The mixture is cooled with ice, and tert-butyldimethylsilyl trifluoromethanesulfonate (4.06 ml) is added to the mixture. Then, the temperature is raised to room temperature, and the whole is stirred overnight. Diethyl ether is added to the reaction mixture, and the whole is washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine successively, and the organic layer is dried over anhydrous magnesium sulfate. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (4.21 g).

Workup

  1. additionis added to the mixture
  2. washthe whole is washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine successively
  3. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer is concentrated under reduced pressure
  5. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-83f77c37fb4b453e9617778a68ece08f
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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