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Sodium Hydroxide → (2-(((4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)butyl)hydroxyphosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamide

HRID 1489792
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1489792
[C:1]1([NH:7][C:8](=[O:45])[C@H:9]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH:10][C:11](=[O:40])[CH:12]([CH2:21][P:22]([CH2:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:39])([O:24]C)=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.Cl>[C:1]1([NH:7][C:8](=[O:45])[C@H:9]([CH2:41][CH:42]([CH3:43])[CH3:44])[NH:10][C:11](=[O:40])[CH:12]([CH2:21][P:22]([CH2:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:39])([OH:24])=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 57286101(2-(((4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)butyl)methoxyphosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamide

Produkt 1

HCID 57084392(2-(((4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)butyl)hydroxyphosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric Acid
Lösungsmittel
HCID 887MethanolLösungsmittel

Versuchsvorschrift

(2-(((4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)butyl)methoxyphosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamide (0.31 g, 0.49 mmol) from Step C was dissolved in methanol (10 mL). The solution was cooled in an ice bath and 2N aqueous sodium hydroxide (5 mL, 10 mmol) was added. The solution was allowed to warm to room temperature and was stirred for an additional 12 h before being diluted with 2N aqueous hydrochloric acid (40 mL) and extracted with ethyl acetate (75 mL). The organic extract was washed with saturated aqueous sodium chloride (25 mL), dried (sodium sulfate), and evaporated. The crude product was purified by high pressure liquid chromatography on a.22 mm×25 cm reverse phase column (Whatman ODS-3, Partisil 10) eluting with 45% acetonitrile/55% water/0.05% trifluoroacetic acid (flow rate of 20 mL/min, detection at 250 nm). Evaporation of appropriate fractions gave 264 mg the desired product (88% yield) as a colorless brittle foam.

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. extractionextracted with ethyl acetate (75 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated aqueous sodium chloride (25 mL)
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. customThe crude product was purified by high pressure liquid chromatography on a
  8. wash22 mm×25 cm reverse phase column (Whatman ODS-3, Partisil 10) eluting with 45% acetonitrile/55% water/0.05% trifluoroacetic acid (flow rate of 20 mL/min, detection at 250 nm)
  9. customEvaporation of appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-f84e7dd3954249e09a33a82f8f7a1f88
Quelldatensatz
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05679700

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