Trifluoroacetic acid → HCID 69952803, 화합물

HRID 2268163노트

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HRID 2268163 반응식
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27]C(C)(C)C)=[O:26])[CH2:21][CH2:20]2)=[N:9]1.[CH2:32](N(CC)CC)C.[CH2:39](Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:3]([OH:5])(=[O:4])/[CH:2]=[CH:32]\[C:25]([OH:27])=[O:26].[C:40]1([CH2:39][N:22]2[CH2:23][CH2:24][CH:19]([CH2:18][CH2:17][C:10]3[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[O:8][N:9]=3)[CH2:20][CH2:21]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 100195501-Piperidinecarboxylic acid, 4-(2-(1,2-benzisoxazol-3-yl)ethyl)-, 1,1-dimethylethyl ester

생성물 1

HCID 69952803HCID 69952803, 화합물수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Trifluoroacetic acid (TFA) (7 mL) was added dropwise to a cold (0° C.) solution of the piperidine formed in step d (0.50 g, 1.51 mmol) in methylene chloride (7 mL). The resulting solution was stirred at 0° C. for 30 min. Volatiles were removed under reduced pressure and excess TFA was removed by concentrating from toluene twice. The crude product was redissolved in methylene chloride (10 mL) and then triethylamine (0.42 mL, 3.01 mmol) and benzyl bromide (0.18 mL, 1.51 mmol) were added. The resulting mixture was stirred overnight (15 hours) at room temperature. The mixture was washed with water and brine and dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatography (50% ethyl acetate/hexanes) gave the title compound (free base) (0.350 g, 73%) as a colorless oil.

후처리

  1. customVolatiles were removed under reduced pressure and excess TFA
  2. customwas removed
  3. concentrationby concentrating from toluene twice
  4. dissolutionThe crude product was redissolved in methylene chloride (10 mL)
  5. stirringThe resulting mixture was stirred overnight (15 hours) at room temperature
  6. washThe mixture was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel flash chromatography (50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-0086f865c069466b87d99b71e56f727e
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326382B1

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