Tetrabutylammonium Fluoride → HCID 58573813, compound

HRID 932196Notes

Reaction equation

HRID 932196 reaction equation
[Si]([O:18][CH2:19][C@@H:20]([N:23]1[C@H:28]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[C@@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[CH2:26][C@@:25]([CH:44]2[CH2:46][CH:45]2[C:47]([OH:49])=[O:48])([CH3:43])[C:24]1=[O:50])[CH2:21][CH3:22])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:42][C:38]1[CH:37]=[C:36]([C@@H:27]2[C@@H:28]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[N:23]([C@@H:20]([CH2:21][CH3:22])[CH2:19][OH:18])[C:24](=[O:50])[C@:25]([CH:44]3[CH2:46][CH:45]3[C:47]([OH:49])=[O:48])([CH3:43])[CH2:26]2)[CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 67999602HCID 67999602, compound

Product 1

HCID 58573813HCID 58573813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the acid from Example 248, Step F (10 mg, 0.014 mmol) in THF (0.2 mL) was added TBAF (0.1 mL, 1.0 M solution in THF). After 30 minutes more TBAF (0.1 mL, 1.0 M solution in THF) was added and the reaction was stirred at rt for 3 hours. After this time the reaction was partitioned between EtOAc (30 mL) and 1M aqueous HCl (5 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by reverse phase HPLC (Sunfire Prep C18 OBD 10 μm column, gradient elution of 20% MeCN in water to 80% MeCN in water over a 30 min period, where both solvents contain 0.1% TFA) to give the title compound.

Workup

  1. customAfter this time the reaction was partitioned between EtOAc (30 mL) and 1M aqueous HCl (5 mL)
  2. dry with materialThe separated organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe resulting residue was purified by reverse phase HPLC (Sunfire Prep
  6. washC18 OBD 10 μm column, gradient elution of 20% MeCN in water to 80% MeCN in water over a 30 min period, where both solvents

Sources & evidence

ORD record
ord-b0735f37ea2b41c9bb21a53a0c69cf10
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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