Triethylamine → HCID 10950646, compound

HRID 368780Notes

Reaction equation

HRID 368780 reaction equation
[S:1]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)([O:4][CH2:5][C@H:6]([OH:17])[C@H:7]([CH3:16])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:3])=[O:2].C(N(CC)CC)C.[Si:32](OS(C(F)(F)F)(=O)=O)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>C(Cl)Cl>[S:1]([C:18]1[CH:19]=[CH:20][C:21]([CH3:22])=[CH:23][CH:24]=1)([O:4][CH2:5][C@H:6]([O:17][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C@H:7]([CH3:16])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 15428282HCID 15428282, compound

Product 1

HCID 10950646HCID 10950646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tosylate 18 (100 g, 0.29 mol) and triethylamine (81.0 mL, 0.58 mol) in CH2Cl2 (1200 mL) was treated with neat TBS-OTf (99 mL, 0.43 mol) dropwise with continued stirring for another 20 min. The reaction was washed twice with brine, dried over MgSO4 and concentrated to dryness. The oil was dissolved in a minimal amount of hexanes and filtered over a silica pad, eluting with hexanes:EtOAc (9:1) to yield the title compound as a slightly amber oil, 134 g.

Workup

  1. washThe reaction was washed twice with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness
  4. dissolutionThe oil was dissolved in a minimal amount of hexanes
  5. filtrationfiltered over a silica pad
  6. washeluting with hexanes:EtOAc (9:1)

Sources & evidence

ORD record
ord-7a91027d88164eb79ef4ba3fc35b7d3a
Source dataset
uspto-grants-2000_10
Patent number
US06133457

Reaction notes

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