Trifluoroacetic acid → 2-(5-((2,2-Difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

HRID 471099Notes

Reaction equation

HRID 471099 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1([F:54])[CH2:29][N:28]([C:30]([C:32]2[N:33]=[C:34]([CH:37]([CH3:39])[CH3:38])[S:35][CH:36]=2)=[O:31])[CH2:27][C:26]2([CH2:44][CH2:43][N:42]([CH2:45][C:46]3[S:47][CH:48]=[C:49]([CH2:51][CH2:52][OH:53])[CH:50]=3)[CH2:41][CH2:40]2)[O:25]1.FC(F)(F)C(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:54][C:24]1([F:23])[CH2:29][N:28]([C:30]([C:32]2[N:33]=[C:34]([CH:37]([CH3:38])[CH3:39])[S:35][CH:36]=2)=[O:31])[CH2:27][C:26]2([CH2:44][CH2:43][N:42]([CH2:45][C:46]3[S:47][CH:48]=[C:49]([CH2:51][CH:52]=[O:53])[CH:50]=3)[CH2:41][CH2:40]2)[O:25]1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989282(2,2-Difluoro-9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 579890332-(5-((2,2-Difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)thiophen-3-yl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin periodinane (0.20 g) was added to stirred solution of (2,2-difluoro-9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 51, step b) (0.15 g) and trifluoroacetic acid (0.031 mL) in DCM (4 mL). After 40 min, the reaction mixture was treated with aqueous saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (30 mL). The mixture was extracted twice with ethyl acetate, the combined organics were washed with saturated sodium bicarbonate solution, acetic acid (0.08 mL) was added, then the solvent was dried over sodium sulphate, filtered, and evaporated in vacuo. Yield 0.19 g. Used directly.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. washthe combined organics were washed with saturated sodium bicarbonate solution, acetic acid (0.08 mL)
  3. additionwas added
  4. dry with materialthe solvent was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-de4ee2b48077449f85e562e6a30a228d
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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