Trifluoroacetic acid → 2-(2,6-Difluoro-3-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)acetaldehyde

HRID 471080Notes

Reaction equation

HRID 471080 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[C:36]([CH2:37][CH2:38][OH:39])=[C:35]([F:40])[CH:34]=[CH:33][C:10]=1[CH2:11][N:12]1[CH2:32][CH2:31][C:15]2([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]3[N:24]=[C:25]([CH:28]([CH3:30])[CH3:29])[S:26][CH:27]=3)=[O:22])[CH2:16]2)[CH2:14][CH2:13]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[C:10]([CH2:11][N:12]2[CH2:32][CH2:31][C:15]3([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]4[N:24]=[C:25]([CH:28]([CH3:30])[CH3:29])[S:26][CH:27]=4)=[O:22])[CH2:16]3)[CH2:14][CH2:13]2)=[CH:33][CH:34]=[C:35]([F:40])[C:36]=1[CH2:37][CH:38]=[O:39]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57988951(9-(2,4-Difluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 579893052-(2,6-Difluoro-3-((4-(2-isopropylthiazole-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 (0.11 mL) was added to a solution of (9-(2,4-difluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 45, step c) (0.7 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.93 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) was then added and the mixture stirred for 10 min. The aqueous layer was separated and extracted with ethyl acetate (20 mL). The combined organics were washed with brine, acidified with a few drops of acetic acid, the mixture dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a clear gum. Yield 0.64 g.

Workup

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

Sources & evidence

ORD record
ord-74c74ad54e674937a8c57fcb87ddcb1d
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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