Tetrabutylammonium Fluoride → (Z)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester

HRID 1058419Notes

Reaction equation

HRID 1058419 reaction equation
[CH3:1][O:2][C:3](=[O:42])/[C:4](/[NH:13][C:14](=[O:41])[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][Si](C(C)(C)C)(C)C)[CH:27]=2)=[O:23])=[CH:17][C:16]=1[CH3:40])=[CH:5]/[C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[CH3:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:42])/[C:4](/[NH:13][C:14](=[O:41])[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[O:23])=[CH:17][C:16]=1[CH3:40])=[CH:5]/[C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[CH3:12]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70030107(Z)-2-[[4-[[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzyl]amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester

Product 1

HCID 59038345(Z)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl esterYield 102.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (Z)-2-[[4-[[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzyl]amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester (47 mg, 0.0773 mmol) in THF (1 mL) was added a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.085 mmol, 85 μL) and the reaction was stirred for 3 days at ambient temperature. The reaction was diluted with ethyl acetate and was then washed with in turn with water and brine. The organic layer was dried (MgSO4), filtered and evaporated in vacuo to yield 39 mg of (Z)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2,6-dimethylbenzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester as a yellow solid (quantitative yield).

Workup

  1. washwas then washed with in turn with water and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f8682905c4f74675a6189c4548920df2
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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