Pyridine → (2S)-1-Acetamido-3-chloropropan-2-yl acetate

HRID 8521

반응식

HRID 8521 반응식
Cl.[NH2:2][CH2:3][C@H:4]([OH:7])[CH2:5][Cl:6].[C:8](OC(=O)C)(=[O:10])[CH3:9].N1[CH:20]=[CH:19]C=CC=1.C(=O)([O-])[O-:22].[K+].[K+]>C(Cl)Cl.O>[C:8]([O:7][C@H:4]([CH2:5][Cl:6])[CH2:3][NH:2][C:19](=[O:22])[CH3:20])(=[O:10])[CH3:9]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 1350101-Amino-3-chloro-2-propanol hydrochloride, (S)-

생성물 1

HCID 7357675(2S)-1-Acetamido-3-chloropropan-2-yl acetate

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매2회

반응 조건

온도
42 °C

실험 절차

To a slurry of (S)-1-amino-3-chloro-2-propanol hydrochloride (500 g, 3.43 mol) in methylene chloride (1.54 kg) and acetic anhydride (803 g, 7.87 mol) is added pyridine (340 g, 4.3 mol) over 1 h while maintaining 38 to 46° C. The mixture is then stirred at 21 to 46° C. for 22 h. Water (600 ml) is added at 22 to 24° C. then aqueous potassium carbonate (47 wt %, 2.0 kg, 6.80 mol) while maintaining 6 to 11° C. Water (600 ml) and methylene chloride (600 ml) are added and the phases separated at 24° C. The aqueous is washed with methylene chloride (600 ml) and the combined organics concentrated under reduced pressure to 1.3 liter total volume. Toluene (2×1.0 liter) was added and the mixture concentrated to 1.4 liter after each addition. The mixture is cooled to 24° C. and isooctanes (2.3 liter) added. The resultant slurry is cooled to 0° C. and the precipitate collected by vacuum filtration, washed with isooctanes (700 ml) and dried in a nitrogen stream to give the title compound. This compound can also be prepared according to the procedures disclosed in WO 9924393 or Tetrahedron Letters, Vol. 37, No. 44, pp. 7937-7940.

후처리

  1. customthe phases separated at 24° C
  2. washThe aqueous is washed with methylene chloride (600 ml)
  3. concentrationthe combined organics concentrated under reduced pressure to 1.3 liter total volume
  4. additionToluene (2×1.0 liter) was added
  5. concentrationthe mixture concentrated to 1.4 liter
  6. additionafter each addition
  7. temperatureThe mixture is cooled to 24° C.
  8. additionisooctanes (2.3 liter) added
  9. temperatureThe resultant slurry is cooled to 0° C.
  10. filtrationthe precipitate collected by vacuum filtration
  11. washwashed with isooctanes (700 ml)
  12. customdried in a nitrogen stream

출처 및 근거

ORD 기록
ord-ce27fe380dda453696f70618851eb0ac
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087784B2

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