Dimethylformamide → (+)-4,5-dihydro-1-[[[(2,2-dimethyl-1-oxopropoxy)methoxy](4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, phenylmethyl ester

HRID 1757941노트

반응식

HRID 1757941 반응식
[OH:1][P:2]([CH2:14][C:15]([N:17]1[CH:21]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:20][C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:18]1)=[O:16])([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:3].CN(C)C=O.[C:43]([O:49][CH2:50]Cl)(=[O:48])[C:44]([CH3:47])([CH3:46])[CH3:45].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:45][C:44]([CH3:47])([CH3:46])[C:43](=[O:48])[O:49][CH2:50][O:3][P:2]([CH2:14][C:15]([N:17]1[CH:21]([C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[CH2:20][C:19]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[N:18]1)=[O:16])([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:1]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 86738774(+)-4,5-dihydro-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, phenylmethyl ester

생성물 1

HCID 86738775(+)-4,5-dihydro-1-[[[(2,2-dimethyl-1-oxopropoxy)methoxy](4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, phenylmethyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4.0 g. of the benzyl ester product from part (c) dissolved in 40 ml. of dry dimethylformamide under argon is treated at ambient temperature with 1.5 g. of chloromethyl pivalate and 1.8 g. of triethylamine. After stirring overnight, the solution is diluted with ethyl acetate and washed with 10% potassium dihydrogen sulfate, water, and saturated brine. The organic solution is dried (MgSO4) and concentrated in vacuo to give the crude product. Flash chromatography on silica gel and elution with ethyl acetate/dichloromethane (1:1) gives homogeneous (+)-4,5-dihydro-1-[[[(2,2-dimethyl-1-oxopropoxy)methoxy](4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, phenylmethyl ester as an oil.

후처리

  1. washwashed with 10% potassium dihydrogen sulfate, water, and saturated brine
  2. dry with materialThe organic solution is dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give the crude product
  5. washFlash chromatography on silica gel and elution with ethyl acetate/dichloromethane (1:1)

출처 및 근거

ORD 기록
ord-da0631405b4045a2befbd45906ad855f
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04371526

반응 노트

불러오는 중…