Sodium Hydroxide → 2,2-Dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-2-(methylsulfanyl-pyrimidine-4-carbonyl)-pyrazolidin-4-yl ester

HRID 1581539

반응식

HRID 1581539 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][NH:12]2)=[O:10])=[CH:4][CH:3]=1.[CH3:23][S:24]([C:27]1[N:32]=[C:31]([C:33](Cl)=[O:34])[CH:30]=[CH:29][N:28]=1)(=O)=O.[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:13][N:12]2[C:33]([C:31]2[CH:30]=[CH:29][N:28]=[C:27]([S:24][CH3:23])[N:32]=2)=[O:34])=[O:10])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 207247362,2-Dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl esterHCID 219921942-Methylsulfonyl-pyrimidine-4-carbonyl chloride

생성물 1

HCID 207247342,2-Dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-2-(methylsulfanyl-pyrimidine-4-carbonyl)-pyrazolidin-4-yl ester수율 96.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2,2-dimethyl-propionic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester, 32, (427 mg, 1.79 mmol) in dichloromethane (3 mL) is added 2-methylsulfonyl-pyrimidine-4-carbonyl chloride (676 mg, 3.58 mmol) followed by dropwise addition of a 1.0 N aqueous solution of sodium hydroxide (6 mL). The mixture is vigorously stirred at room temperature for 12 hours. The reaction is diluted with dichloromethane (25 mL) and washed with water (25 mL). The aqueous layer is back-extracted with dichloromethane (25 mL). The combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (25 mL) and brine (25 mL), dried, filtered and concentrated in vacuo. The resulting crude material is purified over silica (1:1 hexane/ethyl acetate to 100% ethyl acetate) to afford 464 mg (96.6% yield) of the desired product as a brown, viscous oil.

후처리

  1. washwashed with water (25 mL)
  2. extractionThe aqueous layer is back-extracted with dichloromethane (25 mL)
  3. washThe combined organic layers are washed with a saturated aqueous solution of sodium bicarbonate (25 mL) and brine (25 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude material is purified over silica (1:1 hexane/ethyl acetate to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-9760ca086a3c45ccbfa35cf6a07cf08f
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730668B2

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