Triethylamine → HCID 58668515, compound

HRID 574982Notes

Reaction equation

HRID 574982 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].[NH4+].[Cl-]>ClCCl.CN(C)C1C=CN=CC=1>[Si:20]([O:1][CH2:2][CH:3]1[CH2:4][CH2:5][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Product 1

HCID 58668515HCID 58668515, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 391A (43.6 g) and triethylamine (42.3 mL) in dichloromethane (633 mL) was added tert-butyldimethylsilyl chloride (38.1 g) and 4-dimethylaminopyridine (3.09 g) and the reaction was stirred overnight at room temperature. A saturated solution of aqueous NH4Cl was added and the layers were separated. The organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography (Analogix, 0-40% hexanes/ethyl acetate.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was purified by regular phase flash column chromatography (Analogix, 0-40% hexanes/ethyl acetate

Sources & evidence

ORD record
ord-01a098780fb44d40ade99eead1f7ac44
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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