Triethylamine → HCID 53882379, compound

HRID 429732Notes

Reaction equation

HRID 429732 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 g (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 exhaustively extracted 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, yielding the title compound in the form of a yellow oil. TLC: methylene chloride/methanol (95:5) Rf=0.88.

Workup

  1. extractionexhaustively extracted 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-8a5e4c54615149fca4f8a916962534e2
Source dataset
uspto-grants-2001_11
Patent number
US06319917B1

Reaction notes

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