Hydrochloric Acid → HCID 57972811, 화합물

HRID 661446노트

반응식

HRID 661446 반응식
[NH2:1][C@H:2]([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=[O:5].Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl>[Cu](I)I.C1(C)C=CC=CC=1.O.CS(C)=O>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([NH:1][C@H:2]([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=[O:5])=[CH:11][CH:12]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 14731979(3R)-3-Aminopentanoic acid

생성물 1

HCID 57972811HCID 57972811, 화합물

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

(R)-3-Aminovaleric acid (12 kg), 1-bromo-4-trifluoromethylbenzene (34.6 kg), copper iodide (3.9 kg) and potassium carbonate (28.3 kg) were added to dimethylsulfoxide (120 liter), and the mixture was sealed under nitrogen atmosphere and stirred at 100-120° C. for 48 hours. After the reaction mixture was cooled, water (120 liter) and toluene (120 liter) were added, the value of the pH was adjusted to below 3 with addition of hydrochloric acid and the solution was separated. The aqueous layer was extracted with toluene (120 liter) and the combined organic layer was washed with water (120 liter). 25% ammonia water (60 liter) and water (60 liter) were added to the organic layer and extracted. The aqueous layer was adjusted to pH 3-4 with addition of hydrochloric acid and extracted with toluene (120 liter). The filtrate was concentrated in vacuo at 30-70° C. of the bath temperature, n-heptane (24 liter) was added to the residue and concentrated twice to give the titled compound as an oily residue. The product was used in the next step without further purification. MS (APCI) m/z: 262 [M+H]+.

후처리

  1. customthe mixture was sealed under nitrogen atmosphere
  2. temperatureAfter the reaction mixture was cooled
  3. customthe solution was separated
  4. extractionThe aqueous layer was extracted with toluene (120 liter)
  5. washthe combined organic layer was washed with water (120 liter)
  6. addition25% ammonia water (60 liter) and water (60 liter) were added to the organic layer
  7. extractionextracted
  8. additionThe aqueous layer was adjusted to pH 3-4 with addition of hydrochloric acid
  9. extractionextracted with toluene (120 liter)
  10. concentrationThe filtrate was concentrated in vacuo at 30-70° C. of the bath temperature, n-heptane (24 liter)
  11. additionwas added to the residue
  12. concentrationconcentrated twice

출처 및 근거

ORD 기록
ord-c18d51e9ff134c97a19c0956044e4440
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084611B2

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