Trimethylaluminum → Mglu1 C-11

HRID 2422717노트

반응식

HRID 2422717 반응식
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([CH3:18])=[C:16]([NH2:19])[S:15][N:14]=2)=[CH:9][CH:8]=1.[CH3:20][C@@H:21]1[CH2:23][C@H:22]1[C:24](OCC1C=CC=CC=1)=[O:25]>ClCCl>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:17]([CH3:18])=[C:16]([NH:19][C:24]([C@@H:22]3[CH2:23][C@H:21]3[CH3:20])=[O:25])[S:15][N:14]=2)=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 16682925TrimethylaluminumHCID 534010803-(4-Methoxyphenyl)-4-methylisothiazol-5-amineHCID 67180743HCID 67180743, 화합물

생성물 1

HCID 57404255Mglu1 C-11수율 80.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

Add trimethylaluminum (2 M in toluene, 3.59 g, 45.5 mmol) to a 0° C. solution of 3-(4-methoxyphenyl)-4-methylisothiazol-5-ylamine (10.0 g, 45.5 mmol) in dichloromethane (455 mL). Stir 5 min and add benzyl (R,R)-2-methylcyclopropane-carboxylate (8.64 g, 45.5 mmol). Heat to 50° C. with nitrogen flow to remove solvent. The resulting oil is heated at 50° C. for 3 h. Quench with water and dilute with EtOAc (300 mL). Wash with 0.1 N HCl, dry (K2CO3), evaporate, and crystallize from hexane/EtOAc to afford (R,R)—N-[3-(4-methoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide. Yield: 80.4%. ES-MS: m/e 303.0 (m+1). (The mother liquor may be used for further recrystallizations.)

후처리

  1. customto remove solvent
  2. temperatureThe resulting oil is heated at 50° C. for 3 h
  3. customQuench with water
  4. additiondilute with EtOAc (300 mL)
  5. washWash with 0.1 N HCl
  6. dry with materialdry (K2CO3)
  7. customevaporate
  8. customcrystallize from hexane/EtOAc

출처 및 근거

ORD 기록
ord-b40c04fcb93d479c82f7717750b0d3ad
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960419B2

반응 노트

불러오는 중…