Trifluoroacetic acid → 2-(3-Chloro-5-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

HRID 471102Notes

Reaction equation

HRID 471102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([CH2:30][CH2:31][OH:32])[CH:29]=1)[CH2:5][N:6]1[CH2:26][CH2:25][C:9]2([O:14][CH2:13][CH2:12][N:11]([C:15]([C:17]3[N:18]=[C:19]([CH:22]([CH3:24])[CH3:23])[S:20][CH:21]=3)=[O:16])[CH2:10]2)[CH2:8][CH2:7]1.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]=[C:28]([CH2:30][CH:31]=[O:32])[CH:27]=[C:4]([CH2:5][N:6]2[CH2:26][CH2:25][C:9]3([O:14][CH2:13][CH2:12][N:11]([C:15]([C:17]4[N:18]=[C:19]([CH:22]([CH3:23])[CH3:24])[S:20][CH:21]=4)=[O:16])[CH2:10]3)[CH2:8][CH2:7]2)[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 57989350(9-(3-Chloro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 579893542-(3-Chloro-5-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (9-(3-chloro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 52, step c) (0.242 g) in DCM (5 mL) was cooled in ice-water, treated with trifluoroacetic acid (0.059 mL) and stirred for 5 minutes. Dess-Martin periodinane (0.323 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 foam. Yield 0.297 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-0d5b894a5b6e42a5a9b02d5fb7154a9c
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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