Trifluoroacetic acid → HCID 57989369, compound

HRID 1689275Notes

Reaction equation

HRID 1689275 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[C:34]([CH2:35][CH2:36][OH:37])=[C:33]([F:38])[CH:32]=[CH:31][C:10]=1[CH2:11][N:12]1[CH2:30][CH2:29][C:15]2([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]3[S:24][C:25]([CH3:28])=[CH: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[CH2:30][CH2:29][C:15]3([O:20][CH2:19][CH2:18][N:17]([C:21]([C:23]4[S:24][C:25]([CH3:28])=[CH:26][CH:27]=4)=[O:22])[CH2:16]3)[CH2:14][CH2:13]2)=[CH:31][CH:32]=[C:33]([F:38])[C:34]=1[CH2:35][CH:36]=[O:37]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989355HCID 57989355, compound

Product 1

HCID 57989369HCID 57989369, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TFA (0.05 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)(5-methylthiophen-2-yl)methanone (example 34, step a) (0.27 g) in DCM (5 mL) at 0° C. and the resulting mixture stirred for 5 min. Dess-Martin periodinane (0.38 g) was then added and the mixture stirred at RT for 45 min. Saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (20 mL) were then added and the mixture stirred vigorously for 10 min. The aqueous phase was separated and extracted with ethyl acetate (20 mL). The combined organic solutions were washed with brine (20 mL), acidified with a few drops of acetic acid, dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a clear gum. Yield 0.27 g.

Workup

  1. stirringthe mixture stirred at RT for 45 min
  2. stirringthe mixture stirred vigorously 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 (20 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-5ef62be1669c4b418d5a8414427fc9ee
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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