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

HRID 471022Notes

Reaction equation

HRID 471022 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][CH:31]=1)[O:7][CH2:8][CH2:9][N:10]1[CH2:28][CH2:27][C:13]2([O:18][CH2:17][CH2:16][N:15]([C:19]([C:21]3[N:22]=[C:23]([CH3:26])[S:24][CH:25]=3)=[O:20])[CH2:14]2)[CH2:12][CH2:11]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>[CH3:26][C:23]1[S:24][CH:25]=[C:21]([C:19]([N:15]2[CH2:14][C:13]3([CH2:27][CH2:28][N:10]([CH2:9][CH2:8][O:7][C:6]4[CH:5]=[C:4]([CH2:3][CH:2]=[O:1])[CH:31]=[CH:30][CH:29]=4)[CH2:11][CH2:12]3)[O:18][CH2:17][CH2:16]2)=[O:20])[N:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 57989375(9-(2-(3-(2-Hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Product 1

HCID 579889622-(3-(2-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)phenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (9-(2-(3-(2-hydroxyethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 24, step c) (0.152 g) in DCM (5 mL) was cooled in ice-water and treated with trifluoroacetic acid (0.039 mL) and stirred for 5 minutes. Dess-Martin periodinane (0.221 g) was added and the mixture was removed from the cooling bath and stirred at room temperature for 25 minutes. The reaction was quenched by the addition of saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL), and the resulting two-phase mixture was stirred for 10 minutes. The mixture was then extracted twice with ethyl acetate, and the combined organic extracts washed with brine. Acetic acid (0.1 mL) was added, and then the acidified extracts were dried over anhydrous magnesium sulphate and concentrated in vacuo to afford the subtitled compound as a brown gum. Yield 0.118 g.

Workup

  1. customthe mixture was removed from the cooling bath
  2. stirringstirred at room temperature for 25 minutes
  3. customThe reaction was quenched by the addition of saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (5 mL)
  4. stirringthe resulting two-phase mixture was stirred for 10 minutes
  5. extractionThe mixture was then extracted twice with ethyl acetate
  6. washthe combined organic extracts washed with brine
  7. additionAcetic acid (0.1 mL) was added
  8. dry with materialthe acidified extracts were dried over anhydrous magnesium sulphate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cb4a6afdceb4dc3a8d2f8307c6cf752
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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