Triethylamine → HCID 53882379, compound

HRID 583424Notes

Reaction equation

HRID 583424 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:32])[N:14]([CH:16]([CH2:30][OH:31])[CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:15])([CH3:11])([CH3:10])[CH3:9]>CS(C)=O>[C:8]([O:12][C:13](=[O:32])[N:14]([CH:16]([CH:30]=[O:31])[CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:15])([CH3:9])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 53634770HCID 53634770, compound

Product 1

HCID 53882379HCID 53882379, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

17.8 ml (127 mmol) of triethylamine and a solution of 22.8 9 (127 mmol) of sulfur trioxide pyridine complex in 100 ml of dimethyl sulfoxide are added in succession to a solution of 14.5 g (42.5 mmol) of (1-hydroxymethyl-2,2-diphenyl-ethyl)-methyl-carbamic acid tert-butyl ester in 80 ml of dimethyl sulfoxide. After 45 minutes the reaction mixture is poured into ice-water and extracted completely with ether. The combined organic phases are washed twice with 1M potassium hydrogen sulfate, twice with water and once with 1M sodium hydrogen carbonate, dried over sodium sulfate and concentrated by evaporation. The title compound is obtained in the form of a yellow oil. TLC: methylene chloride/methanol (95:5) Rf =0.88; Rt (HPLC)=20.1 min; 1H-NMR (300 MHz, CDCl3, RT) d 9.53 (s, 1H), 7.42-7.16 (m, 10H), 5.35/5.00 (d, 1H), 4.57/4.55 (d, 1H), 2.62/2.54 (s, 3H), 1.50/1.40 (s, 9H).

Workup

  1. extractionextracted completely with ether
  2. washThe combined organic phases are washed twice with 1M potassium hydrogen sulfate, twice with water and once with 1M sodium hydrogen carbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-981d49c72582418c9b2ef9672aae1318
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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