Ethyl Acetate → Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

HRID 40624

반응식

HRID 40624 반응식
COC1C=C(OC)C=CC=1C[N:6]1[C:13](=[O:14])[C@H:12]2[N:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=3)[C:16](=[O:17])[C@@H:7]1[CH2:8][CH:9]=[CH:10][CH2:11]2.C(OCC)(=O)C>FC(F)(F)C(O)=O.C1(SC)C=CC=CC=1.CCCCCCC>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[N:15]1[C:16](=[O:17])[C@H:7]2[NH:6][C:13](=[O:14])[C@@H:12]1[CH2:11][CH:10]=[CH:9][CH2:8]2

참가 물질

6

반응물 2

HCID 8857Ethyl Acetate2회HCID 69230528Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

생성물 1

HCID 69230546Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione

시약·촉매·용매 3

HCID 6422Trifluoroacetic acid용매HCID 7520Thioanisole용매HCID 8900Heptane용매

실험 절차

Z-(1S,6S)-7-(2,4-Dimethoxy-benzyl)-9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione (0.180, 0.406 mmol) was placed in a CEM microwave 10-mL pressure-rated tube and was dissolved in trifluoroacetic acid (4.25 mL) and thioanisol (0.05 mL). The reaction mixture was capped and heated in a CEM discover system laboratory microwave at 120° C. for 0.5 hours. The reaction mixture was poured into a 100 mL round bottom flask and Celite® (approximately 5 g) and ethyl acetate (20 mL) were added. The solvents were removed. The Celite®/reaction mixture was loaded into an Isco solid phase loading cartridge. Flash chromatography was carried out using an Isco Companion automated chromatography system, silica column (12 g), initially holding at 40% ethyl acetate in heptane for 8 column volumes, increasing the ethylacetate concentration to 100% over 3 column volumes, holding at 100% ethyl acetate for 20 more column volumes to yield a residue.

후처리

  1. customThe reaction mixture was capped
  2. temperatureheated in a CEM
  3. customat 120° C.
  4. customfor 0.5 hours
  5. additionThe reaction mixture was poured into a 100 mL round bottom flask
  6. customThe solvents were removed
  7. customThe Celite®/reaction mixture
  8. temperatureincreasing
  9. concentrationthe ethylacetate concentration to 100% over 3 column volumes
  10. customto yield a residue

출처 및 근거

ORD 기록
ord-1069adaef9074f0187f577692185ade6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530475B2

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