TBAF tetrahydrofuran → 2-Amino-5-hydroxymethyl-thiazole-4-carboxylic acid methyl ester

HRID 908638Notes

Reaction equation

HRID 908638 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH2:19])[S:8][C:9]=1[CH2:10][O:11][Si](C(C)(C)C)(C)C)=[O:4].O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH2:19])[S:8][C:9]=1[CH2:10][OH:11])=[O:4]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 597038132-Amino-5-(tert-butyldimethylsilyloxymethyl)-thiazole-4-carboxylic acid methyl ester

Product 1

HCID 597037902-Amino-5-hydroxymethyl-thiazole-4-carboxylic acid methyl esterYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (2.03 g) obtained in Step 1 in tetrahydrofuran (40 ml) was added dropwise, with stirring under ice-cooling, 1.0M tetrabutylammonium fluoride tetrahydrofuran solution (7.38 ml). After stirring at room temperature for 1 hr, the reaction mixture was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1) to give the title compound (1.06 g).

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for 1 hr
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe concentrated residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-efedd6aa05994bc89e426cc4539c8ca7
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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