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

HRID 471064Notes

Reaction equation

HRID 471064 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][OH:54])=[CH:48][C:25]=1[CH2:26][N:27]1[CH2:47][CH2:46][C:30]2([O:35][CH2:34][CH2:33][N:32]([C:36]([C:38]3[N:39]=[C:40]([CH:43]([CH3:45])[CH3:44])[S:41][CH:42]=3)=[O:37])[CH2:31]2)[CH2:29][CH2:28]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:23][C:24]1[CH:51]=[CH:50][C:49]([CH2:52][CH:53]=[O:54])=[CH:48][C:25]=1[CH2:26][N:27]1[CH2:28][CH2:29][C:30]2([O:35][CH2:34][CH2:33][N:32]([C:36]([C:38]3[N:39]=[C:40]([CH:43]([CH3:44])[CH3:45])[S:41][CH:42]=3)=[O:37])[CH2:31]2)[CH2:46][CH2:47]1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989245(9-(2-Fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 579892942-(4-Fluoro-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

Dess-Martin periodinane (0.284 g) was added to a stirred solution of (9-(2-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 40, step b) (0.21 g) and trifluoroacetic acid (0.046 mL) in DCM (5 mL). After 1 h, ethyl acetate (30 mL) was added followed by a mixture of saturated sodium thiosulphate solution (5 mL) and saturated sodium bicarbonate solution (5 mL). The reaction mixture was shaken well and separated. The ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine. Acetic acid (0.07 mL) was added, the solution dried over sodium sulphate, filtered and evaporated in vacuo (bath temperature ˜30° C.) to give the subtitled compound as a gum. Yield 0.2 g. Used directly.

Workup

  1. customseparated
  2. washThe ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine
  3. additionAcetic acid (0.07 mL) was added
  4. dry with materialthe solution dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo (bath temperature ˜30° C.)

Sources & evidence

ORD record
ord-d9592577cf5c4505a628f4a4a1eaff54
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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