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

HRID 471238노트

반응식

HRID 471238 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-27134d34e77147c39d724a073e03ff7f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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