Methyl triflate → HCID 10142201, compound

HRID 1355637Notes

Reaction equation

HRID 1355637 reaction equation
O(C)S(C(F)(F)F)(=O)=O.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[CH3:26][O:27][C:28](=[O:60])[CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][C@H:35]1[C:39](=[O:40])[CH2:38][C@@H:37]([O:41][CH3:42])[C@@H:36]1/[CH:43]=[CH:44]/[CH2:45][CH:46]([C:49]1([CH2:53][C:54]2[S:55][C:56]([Cl:59])=[CH:57][CH:58]=2)[CH2:52][CH2:51][CH2:50]1)[O:47]C>C1(C)C=CC=CC=1>[CH3:26][O:27][C:28](=[O:60])[CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][C@H:35]1[C:39](=[O:40])[CH2:38][C@@H:37]([O:41][CH3:42])[C@@H:36]1/[CH:43]=[CH:44]/[CH2:45][CH:46]([C:49]1([CH2:53][C:54]2[S:55][C:56]([Cl:59])=[CH:57][CH:58]=2)[CH2:50][CH2:51][CH2:52]1)[OH:47]

Participants

5

Reactant 3

HCID 9526Methyl triflateHCID 88675Proton spongeHCID 70031493HCID 70031493, compound

Product 1

HCID 10142201HCID 10142201, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl triflate (145 mg, 09 mmol) was added to a mixture of alcohol 26-H (26 mg, 0.054 mmol) and proton sponge (200 mg, 0.933 mmol) in toluene (5 ml). After 3 days, the mixture was quenched with NaHCO3 (sat) and extracted with CH2Cl2 (3×). The combined organics were washed with 1N HCl, NaHCO3 (sat), brine, dried (Na2SO4) and concentrated in vacuo. FCC (silica gel, 4:1, hexane/EtOAc followed by 2:1, haxane/EtOAc) gave the above named compounds 28 and 29-H.

Workup

  1. customthe mixture was quenched with NaHCO3 (sat)
  2. extractionextracted with CH2Cl2 (3×)
  3. washThe combined organics were washed with 1N HCl, NaHCO3 (sat), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customFCC (silica gel, 4:1, hexane/EtOAc followed by 2:1, haxane/EtOAc) gave the

Sources & evidence

ORD record
ord-4bb7d8031b694c398d2bccfb94057980
Source dataset
uspto-grants-2003_07
Patent number
US06586462B2

Reaction notes

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