phosphenous acid → 3(s)-(4-Chloro-phenyl)-2(s)-ethyl-n-hydroxy-4-morpholin-4-yl-4-oxo-butyramide

HRID 733320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733320
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[C@H:9]([CH2:13][CH3:14])[C:10](O)=[O:11])=[CH:4][CH:3]=1.OP=O.[Si]([O:30][NH2:31])(C)(C)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[C@H:9]([CH2:13][CH3:14])[C:10]([NH:31][OH:30])=[O:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 22497phosphenous acidHCID 2734666O-(Trimethylsilyl)hydroxylamine2×HCID 113133743(S)-(4-Chloro-phenyl)-2(S)-ethyl-4-morpholin-4-yl-4-oxo-butyric acid

Produkt 1

HCID 99279313(s)-(4-Chloro-phenyl)-2(s)-ethyl-n-hydroxy-4-morpholin-4-yl-4-oxo-butyramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The crude acid 1b (310 mg, 0.95 mmol) was dissolved in 5 ml of dichloromethane. HOPO (111 mg, 1 mmol) and MEI (0.159 ml, 1.14 mmol) were added successively. The mixture was stirred for 30 minutes, then TMSONH2 (0.233 ml, 1.9 mmol) was added. After one hour another portion of TMSONH2 (0.233 ml, 1.9 mmol) was added and stirring continued over night. The reaction mixture was filtered (solid contained mostly HOPO) diluted with 20 ml of dichloromethane and extracted twice with 2N-HCl and brine, dried over anhydrous sodium sulfate and evaporated. The crude solid (237 mg, 73%) was purified by preparative HPLC (methanol/water=1/1). Yield: 100 mg (31%).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued over night
  3. filtrationThe reaction mixture was filtered (solid
  4. additiondiluted with 20 ml of dichloromethane
  5. extractionextracted twice with 2N-HCl and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe crude solid (237 mg, 73%) was purified by preparative HPLC (methanol/water=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-d2f47feed4234b039e031033850dfaa3
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589091B2

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