Trifluoroacetic acid → 7-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2,2-dimethylheptanal

HRID 1689468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689468
FC(F)(F)C(O)=O.[OH:8][CH2:9][C:10]([CH3:38])([CH3:37])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:36][CH2:35][C:19]2([O:24][CH2:23][CH2:22][N:21]([C:25]([C:27]3[N:28]=[C:29]([CH:32]([CH3:34])[CH3:33])[S:30][CH:31]=3)=[O:26])[CH2:20]2)[CH2:18][CH2:17]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:32]([C:29]1[S:30][CH:31]=[C:27]([C:25]([N:21]2[CH2:20][C:19]3([CH2:35][CH2:36][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([CH3:38])([CH3:37])[CH:9]=[O:8])[CH2:17][CH2:18]3)[O:24][CH2:23][CH2:22]2)=[O:26])[N:28]=1)([CH3:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 57989082(9-(7-Hydroxy-6,6-dimethylheptyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Produkt 1

HCID 579890537-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2,2-dimethylheptanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (0.048 mL) was added to a solution of (9-(7-hydroxy-6,6-dimethylheptyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone (example 102, step c) (0.28 g) in DCM (15 mL) at 0° C. under argon and the mixture stirred for 5 min before addition of Dess-Martin periodinane (0.39 g). The reaction mixture was stirred at RT for 1 h then was quenched by addition of saturated sodium bisulfite solution (10 mL) and saturated sodium bicarbonate solution (10 mL) then ethyl acetate was added and the mixture stirred for 5 min. The layers were separated and the aqueous solution was extracted with ethyl acetate (×2). The combined organic solutions were washed with saturated sodium bicarbonate solution. Acetic acid (0.053 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 0.33 g.

Aufarbeitung

  1. customthen was quenched by addition of saturated sodium bisulfite solution (10 mL) and saturated sodium bicarbonate solution (10 mL)
  2. additionethyl acetate was added
  3. stirringthe mixture stirred for 5 min
  4. customThe layers were separated
  5. extractionthe aqueous solution was extracted with ethyl acetate (×2)
  6. washThe combined organic solutions were washed with saturated sodium bicarbonate solution
  7. additionAcetic acid (0.053 mL) was added to the organic phase which
  8. dry with materialwas then dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ceefe353231149d99a42d4a87b28c2a4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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