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

HRID 471000Notes

Reaction equation

HRID 471000 reaction equation
C(O)(C(F)(F)F)=O.[OH:8][CH2:9][CH2:10][C:11]1[CH:36]=[CH:35][C:14]([CH2:15][N:16]2[CH2:34][CH2:33][C:19]3([O:24][CH2:23][CH2:22][N:21]([C:25]([C:27]4[N:28]=[C:29]([CH3:32])[S:30][CH:31]=4)=[O:26])[CH2:20]3)[CH2:18][CH2:17]2)=[CH:13][CH:12]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:32][C:29]1[S:30][CH:31]=[C:27]([C:25]([N:21]2[CH2:20][C:19]3([CH2:33][CH2:34][N:16]([CH2:15][C:14]4[CH:13]=[CH:12][C:11]([CH2:10][CH:9]=[O:8])=[CH:36][CH:35]=4)[CH2:17][CH2:18]3)[O:24][CH2:23][CH2:22]2)=[O:26])[N:28]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57988939(9-(4-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Product 1

HCID 579891222-(4-((4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TFA (0.030 mL) was added to a solution of (9-(4-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 16, step b) (0.16 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.245 g) was added and the mixture allowed to warm to room temperature and stirred for 45 min. A mixture of saturated sodium thiosulphate solution (5 mL), saturated sodium bicabonate solution (5 mL) and ethyl acetate (20 mL) was then added and the resulting mixture stirred for 10 min. The aqueous phase was separated and extracted with ethyl acetate (20 mL). The combined organic solutions were washed with brine. AcOH (0.1 mL) was then added and the mixture dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a clear oil which was used immediately. Yield 0.16 g.

Workup

  1. stirringstirred for 45 min
  2. additionwas then added
  3. stirringthe resulting mixture stirred for 10 min
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate (20 mL)
  6. washThe combined organic solutions were washed with brine
  7. additionAcOH (0.1 mL) was then added
  8. dry with materialthe mixture dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-547a428bc1d54503bae3ef8a8ae1f72c
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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