Water → HCID 86687086, compound

HRID 1402233Notes

Reaction equation

HRID 1402233 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:16][CH2:15][CH:14]([C:17]([OH:20])([CH3:19])[CH3:18])[CH2:13][CH2:12]3)=[N:9][N:10]=2)[CH:7]=1.FC(F)(F)S(O[Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])(=O)=O.CCN(CC)CC.O>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:12][CH2:13][CH:14]([C:17]([CH3:18])([O:20][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH3:19])[CH2:15][CH2:16]3)=[N:9][N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 2724529Triisopropylsilyl trifluoromethanesulfonate2×HCID 86687087HCID 86687087, compound

Product 1

HCID 86687086HCID 86687086, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of Intermediate 74a (480 mg, 1.72 mmol), triisopropylsilyl trifluoromethane-sulfonate (0.579 mL, 2.16 mmol) and Et3N (0.361 mL, 2.59 mmol) in dry DCM (5 mL) under N2 was stirred at reflux for 2 h. The mixture was cooled to RT, then Et3N (0.361 mL, 2.59 mmol) and triisopropylsilyl trifluoromethanesulfonate (0.579 mL, 2.16 mmol) were added and the orange solution stirred at reflux for 3 h. To the cooled solution, water (5 mL) was added and the mixture shaken. The aqueous was extracted with DCM (5 mL), then the combined organics passed through a hydrophobic frit and concentrated in vacuo to leave an orange oil. FCC, using 1-3% MeOH in DCM, gave the title compound as a pale yellow solid (592 mg, 79%). LCMS (Method 3): Rt 5.66 min, m/z 435 [MH+].

Workup

  1. temperatureat reflux for 2 h
  2. temperatureat reflux for 3 h
  3. stirringthe mixture shaken
  4. extractionThe aqueous was extracted with DCM (5 mL)
  5. concentrationconcentrated in vacuo
  6. customto leave an orange oil

Sources & evidence

ORD record
ord-53837bd0468e41cdb4f9b7b8498a9950
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…