Trifluoroacetic acid → 10-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)decan-2-one

HRID 471314Notes

Reaction equation

HRID 471314 reaction equation
[OH:1][CH:2]([CH3:32])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:31][CH2:30][C:14]2([O:19][CH2:18][CH2:17][N:16]([C:20]([C:22]3[N:23]=[C:24]([CH:27]([CH3:29])[CH3:28])[S:25][CH:26]=3)=[O:21])[CH2:15]2)[CH2:13][CH2:12]1.FC(F)(F)C(O)=O.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>[CH:27]([C:24]1[S:25][CH:26]=[C:22]([C:20]([N:16]2[CH2:15][C:14]3([CH2:30][CH2:31][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2](=[O:1])[CH3:32])[CH2:12][CH2:13]3)[O:19][CH2:18][CH2:17]2)=[O:21])[N:23]=1)([CH3:29])[CH3:28]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2×HCID 516892Sodium BicarbonateHCID 57988918(9-(9-Hydroxydecyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 5798891310-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)decan-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (9-(9-hydroxydecyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 280, step b) (287 mg) in DCM (10 mL) at 0° C. under nitrogen was added trifluoroacetic acid (0.048 mL). The mixture was stirred for 5 minutes then Dess-Martin periodinane (392 mg) was added. The reaction mixture was stirred at room temperature for 5 hours then a further amount of Dess-Martin periodinane (392 mg) was added at 0° C. then stirred at room temperature for 1.75 h. Saturated sodium thiosulfate solution (20 mL), saturated aqueous sodium bicarbonate solution (20 mL) and ethyl acetate were added and the mixture stirred then the phases separated. The aqueous layer was extracted with ethyl acetate (×2) and the combined organics were washed with saturated aqueous sodium bicarbonate solution. Acetic acid (0.053 mL) was added then the organics were dried over sodium sulfate, filtered and evaporated to afford the titled compound as a yellow gum. Yield 0.338 g.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 hours
  2. stirringthen stirred at room temperature for 1.75 h
  3. stirringthe mixture stirred
  4. customthe phases separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (×2)
  6. washthe combined organics were washed with saturated aqueous sodium bicarbonate solution
  7. additionAcetic acid (0.053 mL) was added
  8. dry with materialthe organics were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-92beddb9c37448e78d8c1e7d1133f0cc
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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