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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Dimethylformamide → (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carbonitrile

HRID 422171
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HRID 422171 반응식
FC(F)(F)S(O[C:7]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]2[C:8]=1[C@@:9]1([CH3:30])[C@H:18]([CH2:19][S:20]2)[C@:17]2([CH3:27])[C@H:12]([C:13]([CH3:29])([CH3:28])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]1)(=O)=O.[CH3:33][N:34](C=O)C>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[C-]#N.[Zn+2]>[CH3:26][O:25][C:23]1[CH:22]=[C:21]2[C:8]([C@@:9]3([CH3:30])[C@H:18]([CH2:19][S:20]2)[C@:17]2([CH3:27])[C@H:12]([C:13]([CH3:29])([CH3:28])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]3)=[C:7]([C:33]#[N:34])[CH:24]=1
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참가 물질

7

반응물 2

HCID 6228DimethylformamideHCID 53241983(1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate

생성물 1

HCID 58294810(1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carbonitrile수율 67%

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매
HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매
HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

A mixture of (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate (32) (0.20 g, 0.40 mmol), Pd(dba)2 (0.037 g, 0.11 mmol), dppf (0.09 g, 0.2 mmol), Zn(CN)2 (0.057 g, 0.48 mmol) in anhydrous DMF (5.0 mL) was placed in a microwave tube. The vessel was heated at 150° C. and 10 psi for 1 h. The reaction was cooled to room temperature, diluted with EtOAc and washed with water. The organic layer was concentrated to dryness. The crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1) to yield (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carbonitrile (77) (0.10 g, 67%) as a white solid.

후처리

  1. customwas placed in a microwave tube
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water
  4. concentrationThe organic layer was concentrated to dryness
  5. customThe crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 10:1)

출처 및 근거

ORD 기록
ord-8166d12d5142454bb284b4f95c4b288f
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101605B2

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