Trifluoroacetic acid → 3-Fluoro-5-[[4-[(2-methyl-4-thiazolyl)carbonyl]-1-oxa-4,9-diazaspiro[5.5]undec-9-yl]methyl]benzeneacetaldehyde

HRID 471007Notes

Reaction equation

HRID 471007 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:32]=[C:33]([CH2:35][CH2:36][OH:37])[CH:34]=1)[CH2:12][N:13]1[CH2:31][CH2:30][C:16]2([O:21][CH2:20][CH2:19][N:18]([C:22]([C:24]3[N:25]=[C:26]([CH3:29])[S:27][CH:28]=3)=[O:23])[CH2:17]2)[CH2:15][CH2:14]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>[F:8][C:9]1[CH:34]=[C:33]([CH2:35][CH:36]=[O:37])[CH:32]=[C:11]([CH2:12][N:13]2[CH2:31][CH2:30][C:16]3([O:21][CH2:20][CH2:19][N:18]([C:22]([C:24]4[N:25]=[C:26]([CH3:29])[S:27][CH:28]=4)=[O:23])[CH2:17]3)[CH2:15][CH2:14]2)[CH:10]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 46240300HCID 46240300, compound

Product 1

HCID 579893163-Fluoro-5-[[4-[(2-methyl-4-thiazolyl)carbonyl]-1-oxa-4,9-diazaspiro[5.5]undec-9-yl]methyl]benzeneacetaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TFA (0.08 mL) was added to a solution of (9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 19, step b) (0.46 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.68 g) was then added and the mixture stirred at RT for 45 min. Saturated sodium thiosulphate solution (5 mL), saturated sodium bicabonate solution (5 mL) and ethyl acetate (20 mL) were then added and the 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, acidified with acetic acid (0.1 mL), dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a yellow gum. Yield 0.4 g.

Workup

  1. stirringthe mixture stirred at RT for 45 min
  2. stirringthe mixture stirred for 10 min
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate (20 mL)
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4c7ef0d045514418a1bdb94bb0cd1090
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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