Water → HCID 67189927, compound

HRID 273205Notes

Reaction equation

HRID 273205 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([C:21]1[CH:22]=[N:23][CH:24]=[N:25][CH:26]=1)[CH:15]=[CH:14]2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[N:23]1[CH:22]=[C:21]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[CH:12]=[C:11]([CH2:10][CH2:9][OH:8])[CH:20]=[CH:19]3)[CH:26]=[N:25][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67104208HCID 67104208, compound

Product 1

HCID 67189927HCID 67189927, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 26C (56 mg, 0.154 mmol) and TBAF.H2O (48 mg, 0.184 mmol, 1.2 equiv.) in THF (3 mL) was stirred at room temperature under a dry nitrogen atmosphere for 30 min. The mixture was then partitioned between ethyl acetate and saturated aqueous Na2CO3. The organic layer was washed with brine then dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give the title compound as an off-white solid (32 mg, 83% yield) which was used in the next step without further purification.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and saturated aqueous Na2CO3
  2. washThe organic layer was washed with brine
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c86286ab8554b3596e6b3923cd3b9d1
Source dataset
uspto-grants-2008_11
Patent number
US07456196B2

Reaction notes

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