Triethylamine → HCID 123820911, compound

HRID 1485116Notes

Reaction equation

HRID 1485116 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)[CH2:3][OH:4].C(N(CC)CC)C.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Si:23]([O:4][CH2:3][CH:2]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)[NH2:1])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11317878(-)-β-Amino-4-iodobenzeneethanol

Product 1

HCID 123820911HCID 123820911, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a mixture of the compound (4.70 g) obtained in step (3) above, 4-dimethylaminopyridine (48.2 mg), triethylamine (4.40 mL) and chloroform (63.2 mL), a solution of tert-butyldimethylchlorosilane (2.38 g) in chloroform (31.6 mL) was added dropwise under cooling with ice and the mixture was stirred at the same temperature for 30 minutes, and then at room temperature for three days. The reaction mixture was concentrated under reduced pressure and water and ethyl acetate were then added. Extraction was conducted with ethyl acetate and the combined organic layers were dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0-98:2) to give the titled compound as a pale yellow oil (4.68 g).

Workup

  1. temperatureunder cooling with ice
  2. waitat room temperature for three days
  3. concentrationThe reaction mixture was concentrated under reduced pressure and water and ethyl acetate
  4. additionwere then added
  5. extractionExtraction
  6. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  7. customThe desiccant was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0-98:2)

Sources & evidence

ORD record
ord-264583208dd74884b8b7c7f76681e763
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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