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

HRID 471242Notes

Reaction equation

HRID 471242 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][C:10]([CH3:40])([CH3:39])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:38][CH2:37][C:21]2([O:26][CH2:25][CH2:24][N:23]([C:27]([C:29]3[N:30]=[C:31]([CH:34]([CH3:36])[CH3:35])[S:32][CH:33]=3)=[O:28])[CH2:22]2)[CH2:20][CH2:19]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:34]([C:31]1[S:32][CH:33]=[C:29]([C:27]([N:23]2[CH2:22][C:21]3([CH2:37][CH2:38][N:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([CH3:40])([CH3:39])[CH:9]=[O:8])[CH2:19][CH2:20]3)[O:26][CH2:25][CH2:24]2)=[O:28])[N:30]=1)([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 57989232(9-(9-Hydroxy-8,8-dimethylnonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Product 1

HCID 579890309-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2,2-dimethylnonanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.059 mL) was added to a solution of (9-(9-hydroxy-8,8-dimethylnonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 103, step c) (0.37 g) in DCM (20 mL) at 0° C. under argon and the mixture stirred for 5 min before addition of Dess-Martin periodinane (0.49 g). The reaction mixture was stirred at RT for 1.25 h then was quenched by addition of saturated sodium thiosulfate solution (20 mL) and saturated sodium bicarbonate solution (20 mL) then ethyl acetate was added and the mixture stirred for 5 min. The phases were separated and the aqueous layer was extracted with ethyl acetate (×2). The combined organic solutions were washed with saturated sodium bicarbonate solution. Acetic acid (0.066 mL) was added to the organic phase which was then dried over sodium sulphate, filtered and evaporated in vacuo to afford the crude subtitled compound as a yellow oil. Yield 0.40 g.

Workup

  1. customthen was quenched by addition of saturated sodium thiosulfate solution (20 mL) and saturated sodium bicarbonate solution (20 mL)
  2. additionethyl acetate was added
  3. stirringthe mixture stirred for 5 min
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (×2)
  6. washThe combined organic solutions were washed with saturated sodium bicarbonate solution
  7. additionAcetic acid (0.066 mL) was added to the organic phase which
  8. dry with materialwas then dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-ab3f841e762143b8bbb4bad277054f70
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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