Triethylamine → 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamide

HRID 20564

Reaction equation

HRID 20564 reaction equation
C(N(CC)CC)C.C([SiH](CC)CC)C.C([O:22][C:23]1[CH:24]=[C:25]([CH:35]=[C:36]([O:38][C@@H:39]([CH3:49])[CH2:40][O:41][Si](C(C)(C)C)(C)C)[CH:37]=1)[C:26]([NH:28][C:29]1[S:30][C:31]([CH3:34])=[CH:32][N:33]=1)=[O:27])C1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:22][C:23]1[CH:24]=[C:25]([CH:35]=[C:36]([O:38][C@@H:39]([CH3:49])[CH2:40][OH:41])[CH:37]=1)[C:26]([NH:28][C:29]1[S:30][C:31]([CH3:34])=[CH:32][N:33]=1)=[O:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 593469333-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide

Product 1

HCID 593469303-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamideYield 21.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.11 mL, 0.79 mmol) and triethylsilane (4.88 mL, 27.3 mmol) were added to palladium (11) acetate (56 mg, 9 mol %) in DCM (14 mL) under an atmosphere of argon. The reaction was stirred for 15 mins then 3-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide (1.4 g, 2.73 mmol) in DCM (14 mL) added dropwise and stirred for a further 48 hours. The reaction was filtered through celite and the filtrate concentrated in vacuo to give a residue which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (0.18 g).

Workup

  1. stirringstirred for a further 48 hours
  2. filtrationThe reaction was filtered through celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a residue which
  5. customwas chromatographed on silica
  6. washeluting with a gradient of 50-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a834994161f4422b977882c441c78710
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Linked notes

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