Trimethylsilyl triflate → HCID 131719535, compound

HRID 741695Notes

Reaction equation

HRID 741695 reaction equation
C(OC([N:8]([CH2:17]/[CH:18]=[CH:19]\[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[CH2:30][CH:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[O:28][N:27]=2)[CH:21]=1)[O:9]C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(Cl)Cl>[F:37][C:34]1[CH:33]=[CH:32][C:31]([CH:29]2[O:28][N:27]=[C:26]([C:22]3[CH:21]=[C:20](/[CH:19]=[CH:18]\[CH2:17][NH:8][OH:9])[CH:25]=[CH:24][CH:23]=3)[CH2:30]2)=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 65367Trimethylsilyl triflateHCID 131719534HCID 131719534, compound

Product 1

HCID 131719535HCID 131719535, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step 4, above (16, 3.2 g, 6.2 mmol) in CH2Cl2 (30 ml) cooled to 0° C., was slowly added trimethylsilyl trifluoromethanesulfonate (2.5 ml, 13.4 mmol) under a nitrogen atmosphere. The reaction mixture was allowed to warm to room temperature and was stirred for 1.5 hours. The reaction mixture was poured carefully into ice cold water (30 ml), the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (30 ml×3). The combined extracts were washed with aqueous NaHCO3 (50 ml) and brine (50 ml), then was dried (MgSO4) and solvent was removed under reduced pressure to afford the title compound (17, (1.8 g, 93% yield) as pale yellow solids.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (30 ml×3)
  3. washThe combined extracts were washed with aqueous NaHCO3 (50 ml) and brine (50 ml)
  4. dry with materialwas dried (MgSO4) and solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-7d96c1652006409e815650861a288971
Source dataset
uspto-grants-1996_09
Patent number
US05552424

Reaction notes

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