1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → HCID 69283084, compound

HRID 1767954Notes

Reaction equation

HRID 1767954 reaction equation
O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:20]([O:24][C:25](=[O:65])[CH2:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH:37]([C:49]3[S:53][C:52]([C:54]4[CH:59]=[CH:58][C:57]([C:60]([F:63])([F:62])[F:61])=[CH:56][CH:55]=4)=[N:51][C:50]=3[CH3:64])[CH2:38][CH2:39][CH2:40][O:41][Si](C(C)(C)C)(C)C)[CH:34]=2)[CH:29]=[CH:28]1)([CH3:23])([CH3:22])[CH3:21]>O1CCCC1>[C:20]([O:24][C:25](=[O:65])[CH2:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH:37]([C:49]3[S:53][C:52]([C:54]4[CH:59]=[CH:58][C:57]([C:60]([F:62])([F:63])[F:61])=[CH:56][CH:55]=4)=[N:51][C:50]=3[CH3:64])[CH2:38][CH2:39][CH2:40][OH:41])[CH:34]=2)[CH:29]=[CH:28]1)([CH3:22])([CH3:23])[CH3:21]

Participants

4

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 69283055HCID 69283055, compound

Product 1

HCID 69283084HCID 69283084, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1 M solution of tetrabutylammonium fluoride hydrate (30 μl, 30 μmol) was added to an ice-cooled solution of [rac]-(6-[4-(tert-butyl-dimethyl-silanyloxy)-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-butoxy}-indol-1-yl)-acetic acid tert-butyl ester (17 mg, 25 μmol) in tetrahydrofuran (0.5 ml). The ice bath was removed and the solution stirred for 30 min at ambient temperature. Ethyl acetate was added and the solution was washed with 1 N HCl. The aqueous layer was extracted with ethyl acetate and the combined extracts were washed two times with brine and dried over sodium sulfate. Evaporation of the solvent gave 14 mg (25 μmol, quant.) of the title compound as yellow oil.

Workup

  1. customThe ice bath was removed
  2. additionEthyl acetate was added
  3. washthe solution was washed with 1 N HCl
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined extracts were washed two times with brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bf0f4cc8f6b24b0c8b81758fe9be8727
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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