Trimethylphosphine → HCID 58460159, 화합물

HRID 1946475

반응식

HRID 1946475 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]3[CH:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][C:13]=3[N:12]=[C:11]2[CH:21]([CH3:23])[CH3:22])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:24]([O:26][C:27]([CH:29]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:28])[CH3:25].CP(C)C.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.CC1CCCO1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]3[CH:15]([C:29]([C:35]([O:37][CH2:38][CH3:39])=[O:36])([C:27]([O:26][CH2:24][CH3:25])=[O:28])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:16][CH2:17][CH2:18][CH2:19][C:13]=3[N:12]=[C:11]2[CH:21]([CH3:23])[CH3:22])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

7

반응물 4

HCID 68983TrimethylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 80471Triethyl methanetricarboxylateHCID 584601473-[(3,4-Dichlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-ol

생성물 1

HCID 58460159HCID 58460159, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 73012-Methyltetrahydrofuran용매

실험 절차

To a suspension of Intermediate 8 (270 mg) and triethylmethanetricarboxylate (0.324 ml) in toluene (4 ml) and methyltetrahydrofuran (4.00 ml), stirred at RT under an inert atmosphere of nitrogen, was added trimethylphosphine, 1M in toluene (1.529 ml). The resulting solution was cooled to −78° C. and diisopropyl azodicarboxylate (0.301 ml) was added dropwise via syringe and the reaction was stirred at −78° C. for 45 mins. The reaction mixture was removed from the cold bath and allowed to warm to RT and stirred under N2 atmosphere overnight. Reaction mixture concentrated slowly in vacuo using the rotavapor with the water bath at 50° C. The residue was taken up in DCM (20 ml) and washed with water (20 mL). The 2 phases were separated; the aqueous was extracted again with DCM (20 mL). The organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified by silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (435 mg).

후처리

  1. temperatureThe resulting solution was cooled to −78° C.
  2. stirringthe reaction was stirred at −78° C. for 45 mins
  3. customThe reaction mixture was removed from the cold bath
  4. temperatureto warm to RT
  5. stirringstirred under N2 atmosphere overnight
  6. customReaction mixture
  7. concentrationconcentrated slowly in vacuo
  8. customat 50° C
  9. washwashed with water (20 mL)
  10. customThe 2 phases were separated
  11. extractionthe aqueous was extracted again with DCM (20 mL)
  12. customdried (hydrophobic frit)
  13. concentrationconcentrated under vacuum
  14. customThe residue was purified by silica using a cyclohexane
  15. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-626ea5e6508c4a4c8b59d6f5ceb35b79
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399444B2

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