Hydrofluoric Acid → HCID 58296224, compound

HRID 552758Notes

Reaction equation

HRID 552758 reaction equation
[S:1](=[O:36])(=[O:35])([O:3][CH2:4][C@@H:5]1[C@@H:9]([O:10][Si](C(C)(C)C)(C)C)[CH2:8][C@H:7]([N:18]2[C:26]3[CH:25]=[CH:24][N:23]=[C:22]([NH:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:21]=3[CH:20]=[CH:19]2)[O:6]1)[NH2:2].F>C1COCC1.N1C=CC=CC=1.N1C=CC=CC=1.CCOC(C)=O>[S:1](=[O:36])(=[O:35])([O:3][CH2:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][C@H:7]([N:18]2[C:26]3[CH:25]=[CH:24][N:23]=[C:22]([NH:27][CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:21]=3[CH:20]=[CH:19]2)[O:6]1)[NH2:2]

Participants

6

Reactant 2

HCID 14917Hydrofluoric AcidHCID 86607331HCID 86607331, compound

Product 1

HCID 58296224HCID 58296224, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 8857Ethyl AcetateSolventHCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of ((2R,3S,5R)-5-[4-(benzylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydrofuran-2-yl)methyl sulfamate (0.0300 g, 0.0563 mmol) in THF/pyridine (1 mL, 1:1) was added hydrofluoric acid in pyridine (3 drops) and stirred overnight. The reaction was diluted with EtOAc (5 mL) and quenched with saturated aq NaHCO3 (10 mL). The aq layer was extracted with EtOAc (3×10 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude material was purified by preparative plate chromatography (10% MeOH/EtOAc) to give the final compound (0.00590 g, 25%).

Workup

  1. customquenched with saturated aq NaHCO3 (10 mL)
  2. extractionThe aq layer was extracted with EtOAc (3×10 mL)
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by preparative plate chromatography (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-6b5330e0f13c40d799d38fca679e59c6
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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