Trifluoroacetic acid → HCID 57989191, compound

HRID 1689394Notes

Reaction equation

HRID 1689394 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[CH2:27][CH2:26][C:10]3([O:15][CH2:14][CH2:13][N:12]([C:16]([C:18]4[N:19]=[C:20]([CH:23]([CH3:25])[CH3:24])[S:21][CH:22]=4)=[O:17])[CH2:11]3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[CH2:30][CH2:31][OH:32].FC(F)(F)C(O)=O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[CH2:27][CH2:26][C:10]3([O:15][CH2:14][CH2:13][N:12]([C:16]([C:18]4[N:19]=[C:20]([CH:23]([CH3:24])[CH3:25])[S:21][CH:22]=4)=[O:17])[CH2:11]3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[CH2:30][CH:31]=[O:32]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 57989207(9-(4-Chloro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 57989191HCID 57989191, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (9-(4-chloro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 75, step d) (0.152 g) in DCM (5 mL) was cooled in ice-water, treated with trifluoroacetic acid (0.049 mL) and stirred for 5 minutes. Dess-Martin periodinane (0.205 g) was added, then the mixture was removed from the cooling bath and stirred at room temperature for 30 minutes. The solution was diluted with saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL) and the resulting mixture was stirred vigorously for 10 minutes. The mixture was then extracted twice with ethyl acetate, the combined organic phases were washed with brine, acidified with acetic acid (0.1 mL), dried over anhydrous magnesium sulphate and concentrated in vacuo to give the crude subtitled compound as a yellow gum. Yield 0.197 g.

Workup

  1. customthe mixture was removed from the cooling bath
  2. stirringstirred at room temperature for 30 minutes
  3. additionThe solution was diluted with saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL)
  4. stirringthe resulting mixture was stirred vigorously for 10 minutes
  5. extractionThe mixture was then extracted twice with ethyl acetate
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried over anhydrous magnesium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-740885c7df4d4700a28b8fa0da93c048
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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