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

HRID 471314노트

반응식

HRID 471314 반응식
[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]

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2회HCID 516892Sodium BicarbonateHCID 57988918(9-(9-Hydroxydecyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-92beddb9c37448e78d8c1e7d1133f0cc
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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