Triethylamine → HCID 68978614, compound

HRID 736862Notes

Reaction equation

HRID 736862 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([N:22](CC)CC)C.ClC(OCC)=O.[NH4+].[OH-]>O1CCCC1>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH2:22])=[O:19])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 21685535HCID 21685535, compound

Product 1

HCID 68978614HCID 68978614, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-tert-butyldimethylsilyloxyphenyl)propionic acid (2.13 g, 7.71 mmol) prepared in 3) was dissolved in tetrahydrofuran (32 ml) in nitrogen atmosphere, and triethylamine (1.16 ml, 8.41 mmol) and ethyl chloroformate (0.726 ml, 8.41 ml) were dropwise added under cooling with ice, followed by stirring for 30 minutes. Then, a 28% ammonia aqueous solution was dropwise added, followed by stirring for 5 minutes. The reaction solution was concentrated under reduced pressure, and water was added to the residue, followed by extraction with ethyl acetate twice. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 3-(4-tert-butyldimethylsilyloxyphenyl)propionic acid amide (1.60 g, 76%) as colorless solid.

Workup

  1. additionwere dropwise added
  2. temperatureunder cooling with ice
  3. stirringby stirring for 5 minutes
  4. concentrationThe reaction solution was concentrated under reduced pressure, and water
  5. additionwas added to the residue
  6. extractionfollowed by extraction with ethyl acetate twice
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ab19e855a0bf48f5afa73da4bae4d4de
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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