Phosphate → (S)-7,8-dihydro-2,9-dimethoxy-7-methyl-6-phenanthridinol trifluoromethanesulfonate

HRID 963268노트

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HRID 963268 반응식
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=O)[C:26]3[C@@H:25]([CH3:33])[CH2:24][C:23]([O:34][CH3:35])=[CH:22][C:21]=3[C:20]=2[CH:19]=1.C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.P([O-])([O-])([O-])=O>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:27]1[N:28]=[C:29]2[C:20](=[C:21]3[C:26]=1[C@@H:25]([CH3:33])[CH2:24][C:23]([O:34][CH3:35])=[CH:22]3)[CH:19]=[C:18]([O:17][CH3:16])[CH:31]=[CH:30]2)(=[O:5])=[O:4]

참가 물질

6

반응물 4

HCID 1061PhosphateHCID 67749Trifluoromethanesulfonic anhydrideHCID 685102,6-Di-tert-butylpyridineHCID 11043868(S)-7,8-dihydro-2,9-dimethoxy-7-methyl-6(5H)-phenanthridinone

생성물 1

HCID 18660709(S)-7,8-dihydro-2,9-dimethoxy-7-methyl-6-phenanthridinol trifluoromethanesulfonate수율 86.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

Trifluoromethanesulfonic anhydride (3.80 mL, 22.4 mmol, 1.10 equiv) was added via syringe to a suspension of (S)-7,8-dihydro-2,9-dimethoxy-7-methyl-6(5H)-phenanthridinone (10, 5.52 g, 20.3 mmol, 1 equiv) and 2.6-di-t-butylpyridine (6.10 mL, 27.1 mmol, 1.33 equiv) in dichloromethane (400 mL) at -78° C. The cold suspension was allowed to warm to 23° C. over 30) min and was stirred at that temperature for 15 min. Solids were observed to dissolve as the reaction proceeded. The reaction mixture was poured into aqueous phosphate buffer solution (pH 7, 0.05M in sodium hydrogen phosphate and 0.05M in potassium dihydrogen phosphate, 200 mL). The aqueous layer was separated and further extracted with two 200-mL portions of dichloromethane. The combined organic layers were dried over sodium sulfate and were concentrated in vacuo. The residue was purified by flash column chromatography (40% dichloromethane-hexanes) to provide (S)-7,8-dihydro-2,9-dimethoxy-7-methyl-6-phenanthridinol trifluoromethanesulfonate (ester) (12) as an off-white solid (mp 129.5°-130.5° C., 7.09 g, 86%). ##STR23##

후처리

  1. dissolutionto dissolve as the reaction
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with two 200-mL portions of dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationwere concentrated in vacuo
  6. customThe residue was purified by flash column chromatography (40% dichloromethane-hexanes)

출처 및 근거

ORD 기록
ord-655a410c3ba8457d843aef18621dcd22
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763451

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