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

HRID 471187Notes

Reaction equation

HRID 471187 reaction equation
[Cl:1][C:2]1[C:29]([CH2:30][CH2:31][OH:32])=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[CH2:25][CH2:24][C:8]2([O:13][CH2:12][CH2:11][N:10]([C:14]([C:16]3[N:17]=[C:18]([CH:21]([CH3:23])[CH3:22])[S:19][CH:20]=3)=[O:15])[CH2:9]2)[CH2:7][CH2:6]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[C:3]([CH2:4][N:5]2[CH2:25][CH2:24][C:8]3([O:13][CH2:12][CH2:11][N:10]([C:14]([C:16]4[N:17]=[C:18]([CH:21]([CH3:22])[CH3:23])[S:19][CH:20]=4)=[O:15])[CH2:9]3)[CH2:7][CH2:6]2)=[CH:26][CH:27]=[CH:28][C:29]=1[CH2:30][CH:31]=[O:32]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 46240302(9-(2-Chloro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 579889712-(2-Chloro-3-((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-(2-chloro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 80, step e) (0.386 g) in DCM (5 mL) was cooled in ice-water, treated with trifluoroacetic acid (0.125 mL) and stirred for 5 minutes. Dess-Martin periodinane (0.519 g) was added, then the mixture was removed from the cooling bath and stirred at room temperature for 35 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 pale yellow gum. Yield 0.494 g.

Workup

  1. customthe mixture was removed from the cooling bath
  2. stirringstirred at room temperature for 35 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-f087f393193a45a8a607b5852012bb43
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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