Triethylamine → HCID 86653293, compound

HRID 1187770Notes

Reaction equation

HRID 1187770 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][OH:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CCOC(C)=O>CS(C)=O>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH:18]=[O:19])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67151537HCID 67151537, compound

Product 1

HCID 86653293HCID 86653293, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of [(S)-3-(4-bromo-phenyl)-1-hydroxymethyl-propyl]-carbamic acid tert-butyl ester (11.5 g) and triethylamine (27.9 ml) in DMSO (70 ml) was added dropwise sulfur trioxide-pyridine complex (16.0 g) while the reaction mixture was cooled in a ice bath. The mixture was then stirred at room temperature for 30 min to afford a yellow solution. The reaction mixture was poured into EtOAc and extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, heptane/EtOAc 3/1) to afford [(S)-3-(4-bromo-phenyl)-1-formyl-propyl]-carbamic acid tert-butyl ester as a yellow oil (7.3 g, 64%). MS (EI): 343 ([{81Br}M]+), 341 ([{79Br}M]+), 287 ([{81Br}M−C4H8]+), 285 ([{79Br}M−C4H8]+), 214 ([{81Br}M−C4H8—CO2]+), 212 ([{79Br}M−C4H8—CO2]+), 171, 169, 103, 57 ([C4H9]+).

Workup

  1. temperaturewas cooled in a ice bath
  2. customto afford a yellow solution
  3. extractionextracted sequentially with water and with saturated brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, heptane/EtOAc 3/1)

Sources & evidence

ORD record
ord-2e094d8f018d46dfa58ab0b8b3ca50c5
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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