Triethylamine → 2-[2-(4-Fluorophenyl)acetyl]-4-(2,2-dimethylpropionyloxy) pyrazolidine-1-carboxylic acid 1-benzyl ester

HRID 22682

반응식

HRID 22682 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](O)=[O:39])=[CH:33][CH:32]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:13][N:12]1[C:38](=[O:39])[CH2:37][C:34]1[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 207247484-(2,2-Dimethylpropionyloxy)pyrazolidine-1-carboxylic acid 1-benzyl ester

생성물 1

HCID 207247472-[2-(4-Fluorophenyl)acetyl]-4-(2,2-dimethylpropionyloxy) pyrazolidine-1-carboxylic acid 1-benzyl ester수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

4-(2,2-Dimethylpropionyloxy)-pyrazolidine-1-carboxylic acid 1-benzyl ester, 30, (1.45 g, 4.23 mmol) is dissolved in dichloromethane (21 mL). The solution is cooled to 0° C. and triethylamine (1.30 mL, 9.31 mmol) added dropwise via syringe. The cold bath is removed and the reaction allowed to warm to room temperature and continue stirring 20 minutes. 4-Fluorophenylacetic acid (848 mg, 5.50 mmol) is added. After stirring for 5 minutes, the reaction mixture is transferred via cannula into a solution of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrogen chloride in dichloromethane (21 mL) maintained at 0° C. The reaction is allowed to stir and gradually warm to room temperature over 12 hours. The reaction is washed with a 5% aqueous solution of Na2CO3 (2×50 mL). The combined aqueous layers are extracted several times with dichloromethane (50 mL) and the combined organic layers washed with brine, dried, filtered and concentrated in vacuo. The crude product is purified over silica (2:1 to 1:1 hexane/ethyl acetate) to afford 1.71 g (91% yield) of the desired product as a white solid.

후처리

  1. customThe cold bath is removed
  2. temperatureto warm to room temperature
  3. stirringAfter stirring for 5 minutes
  4. temperaturemaintained at 0° C
  5. stirringto stir
  6. temperaturegradually warm to room temperature over 12 hours
  7. washThe reaction is washed with a 5% aqueous solution of Na2CO3 (2×50 mL)
  8. extractionThe combined aqueous layers are extracted several times with dichloromethane (50 mL)
  9. washthe combined organic layers washed with brine
  10. customdried
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe crude product is purified over silica (2:1 to 1:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-21bba38f12764b9f8e18cb2a3fb78b24
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849627B2

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