Triethylamine → HCID 86603187, compound

HRID 1818961Notes

Reaction equation

HRID 1818961 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:7]1[S:11][C:10]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[O:14])=[N:9][CH:8]=1)[CH2:5][OH:6].C(N(CC)CC)C.FC(F)(F)S(O[Si:40]([CH:47]([CH3:49])[CH3:48])([CH:44]([CH3:46])[CH3:45])[CH:41]([CH3:43])[CH3:42])(=O)=O>ClCCl.C1COCC1>[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:7]1[S:11][C:10]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=2)=[O:14])=[N:9][CH:8]=1)[CH2:5][O:6][Si:40]([CH:47]([CH3:49])[CH3:48])([CH:44]([CH3:46])[CH3:45])[CH:41]([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 86603186HCID 86603186, compound

Product 1

HCID 86603187HCID 86603187, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a mixture of compound 73.1 (1.67 mmol) and triethylamine (2.2 equivalent) in 1:1 dichloromethane/THF (12.0 mL) was added triisopropylsilyl trifluoromethanesulfonate (2.2 equivalents) dropwise at 0° C. After complete consumption of the starting material (TLC 30% EtOAc in hexanes) the reaction mixture is diluted with EtOAc and washed with 0.5 N HCl, saturated sodium bicarbonate, dried and concentrated to give a residue that was purified by flash column chromatography on silica gel (0 to 60% EtOAc in hexanes) to provide 2-{2-[3-(3-trifluoromethyl-phenyl)-ureido]-thiazol-5-yl}-3-triisopropylsilanyloxy-propionic acid methyl ester (compound 73.2) as a foam.

Workup

  1. customAfter complete consumption of the starting material (TLC 30% EtOAc in hexanes) the reaction mixture
  2. additionis diluted with EtOAc
  3. washwashed with 0.5 N HCl, saturated sodium bicarbonate
  4. customdried
  5. concentrationconcentrated
  6. customto give a residue that
  7. customwas purified by flash column chromatography on silica gel (0 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e00f1d0615454244b1aab95fe6bb864e
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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