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

HRID 1689304Notes

Reaction equation

HRID 1689304 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([C:27]1[S:28][CH:29]=[C:30]([C:32]([N:34]2[CH2:39][C:38]3([CH2:44][CH2:43][N:42]([CH2:45][C:46]4[S:47][CH:48]=[C:49]([CH2:51][CH2:52][OH:53])[CH:50]=4)[CH2:41][CH2:40]3)[O:37][CH2:36][CH2:35]2)=[O:33])[N:31]=1)([CH3:26])([CH3:25])[CH3:24].C(O)(C(F)(F)F)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:23]([C:27]1[S:28][CH:29]=[C:30]([C:32]([N:34]2[CH2:39][C:38]3([CH2:40][CH2:41][N:42]([CH2:45][C:46]4[S:47][CH:48]=[C:49]([CH2:51][CH:52]=[O:53])[CH:50]=4)[CH2:43][CH2:44]3)[O:37][CH2:36][CH2:35]2)=[O:33])[N:31]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989044(2-tert-Butylthiazol-4-yl)(9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Product 1

HCID 579892042-(5-((4-(2-tert-Butylthiazole-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 (0.316 g) was added to stirred solution of (2-tert-butylthiazol-4-yl)(9-((4-(2-hydroxyethyl)thiophen-2-yl)methyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 43, step d) (0.23 g) and TFA (0.05 mL) in DCM (5 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 solution was dried over sodium sulphate, filtered, and then evaporated in vacuo to afford the subtitled compound. Yield 0.23 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 solution was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e6ce540fe549461080e3397d63780d6b
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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