Tetrabutylammonium Fluoride → HCID 66849549, compound

HRID 1046421Notes

Reaction equation

HRID 1046421 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:23]#[C:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:8][C:9]=1[NH:10][C@@H:11]([CH3:22])[CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C)C)=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:23]#[C:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:8][C:9]=1[NH:10][C@@H:11]([CH3:22])[CH2:12][CH2:13][OH:14])=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58113978HCID 58113978, compound

Product 1

HCID 66849549HCID 66849549, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-[3-(tert-Butyl-dimethyl-silanoxy)-1-(S)-methyl-propylamino]-5-(3,3-dimethyl-but-1-ynyl)thiophene-2-carboxylic acid methyl ester (8.2 g, 18.24 mmol) was taken up in THF (200 mL). TBAF 1.0M in THF (88.15 mL, 88.15 mmol) was added in 20 mL increments at rt. The reaction was monitored by LC/MS. The reaction was determined to be complete at 30 min. and was quenched with sat NH4Cl(aq) (200 mL). After stirring at it for 1 h. the organics were removed under reduced pressure and treated with EtOAc. The solution was dried over Na2SO4, solids were filtered and the solvent removed under reduced pressure. 5-(3,3-dimethyl-but-1-ynyl)3-(3-hydroxy-1-(S)-methyl-propylamino)-thiophene-2-carboxylic acid methyl ester (4.0 g, 73%) was isolated by silica gel chromatography as a yellow solid.

Workup

  1. customwas quenched with sat NH4Cl(aq) (200 mL)
  2. customorganics were removed under reduced pressure
  3. additiontreated with EtOAc
  4. dry with materialThe solution was dried over Na2SO4, solids
  5. filtrationwere filtered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e4ca5b317db34727a060a895531fc8c8
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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