Triethylamine → HCID 67490982, compound

HRID 1917399Notes

Reaction equation

HRID 1917399 reaction equation
[C:1]([NH:20][CH2:21][CH:22]1[CH:27]([OH:28])[CH2:26][CH2:25][CH2:24][O:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[C:1]([NH:20][CH2:21][CH:22]1[C:27](=[O:28])[CH2:26][CH2:25][CH2:24][O:23]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67490784HCID 67490784, compound

Product 1

HCID 67490982HCID 67490982, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of a sulfur trioxide-pyridine complex (23.7 g, 149 mmol) in dimethyl sulfoxide (150 mL) was added to a solution of 2-(tritylamino)methyl-3,4,5,6-tetrahydro-2H-pyran-3-ol (18.54 g, 49.6 mmol) and triethylamine (45 mL, 323 mmol) in dimethyl sulfoxide (150 mL) in a nitrogen atmosphere at room temperature. The mixture was stirred at the same temperature for 10 hours. The reaction solution was poured into ice water (1 L), followed by extraction with ethyl acetate (2×1 L). Then, the organic layers were combined and washed with water (2×1 L) and brine (1 L). The resulting organic layer was dried over anhydrous sodium sulfate and filtered. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95→10:90→20:80) to give 9.56 g (52%) of the title compound as a colorless transparent gummy solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate (2×1 L)
  2. washwashed with water (2×1 L) and brine (1 L)
  3. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThen, the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95→10:90→20:80)

Sources & evidence

ORD record
ord-856c910cf7b648f892313abee6d7a5d4
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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