2-Methyl-2-butene → (1S,2R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carboxylic acid

HRID 1772337노트

반응식

HRID 1772337 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@@:10]3([CH2:25][C@H:24]3[CH:26]=[O:27])[N:9]=2)=[CH:4][CH:3]=1.CC(=CC)C.Cl([O-])=[O:34].[Na+]>CC(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@@:10]3([CH2:25][C@H:24]3[C:26]([OH:34])=[O:27])[N:9]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86706921(1S,2R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carbaldehyde

생성물 1

HCID 57404934(1S,2R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carboxylic acid

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

To a solution of crude (1S,2R)-4′-(4-chlorophenyl)-2′,3′,9′-trimethylspiro[cyclopropane-1,6′-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carbaldehyde (298 mg, 0.752 mmol) in t-BuOH (5 mL) was added 2-methylbut-2-ene (1055 mg, 15.04 mmol) and a pH 7 buffer solution (5 mL). Then sodium chlorite was added at rt, and the biphasic reaction was vigorously stirred for 3.5 h. When the starting material was entirely consumed, sat. aq. NH4Cl was added, and the product was extracted with DCM/MeOH (19:1) (repeated 3 times). The organic layers were combined, dried over Na2SO4, filtered and concentrated to dryness. The residue was used in the next step without purification. LRMS (M+H)+: 413 m/z.

후처리

  1. customthe biphasic reaction
  2. customWhen the starting material was entirely consumed
  3. additionsat. aq. NH4Cl was added
  4. extractionthe product was extracted with DCM/MeOH (19:1) (repeated 3 times)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was used in the next step without purification

출처 및 근거

ORD 기록
ord-6d662412a1e34ea3a393359a7ea71e3f
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249161B2

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