Water → HCID 86687095, compound

HRID 630810Notes

Reaction equation

HRID 630810 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][CH2:14][C@@H:13]([CH2:17][OH:18])[CH2:12]3)=[N:9][N:10]=2)[CH:7]=1.CCN(CC)CC.FC(F)(F)S(O[Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])(=O)=O.O>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N:11]3[CH2:16][CH2:15][CH2:14][C@@H:13]([CH2:17][O:18][Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])[CH2:12]3)=[N:9][N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 86687094HCID 86687094, compound

Product 1

HCID 86687095HCID 86687095, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Intermediate 77a (233 mg, 0.931 mmol) and Et3N (0.195 mL, 1.40 mmol) in dry DCM (5 mL) at RT under N2, was added triisopropylsilyl trifluoromethanesulfonate (0.313 mL, 1.16 mmol) and the yellow solution stirred at RT for 30 min. 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 fit and concentrated in vacuo to leave a yellow oil. FCC, using 1-5% MeOH in DCM, gave the title compound as a yellow oil (333 mg, 88%). LCMS (Method 3): Rt 5.23 min, m/z 407 [MH+].

Workup

  1. stirringthe mixture shaken
  2. extractionThe aqueous was extracted with DCM (5 mL)
  3. concentrationconcentrated in vacuo
  4. customto leave a yellow oil

Sources & evidence

ORD record
ord-9942f08061d14c8f84dd42d4507ef0a6
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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