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 1757941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757941
[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]

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-da0631405b4045a2befbd45906ad855f
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04371526

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