Acetic Acid → HCID 18727100, Verbindung

HRID 842771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842771
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)([O-:3])=[O:2].[NH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:23]([O:22][C:21](=[O:27])[NH:20][CH2:19][CH2:18][NH:17][CH:13]1[CH2:14][CH2:15][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:11][CH2:12]1)([CH3:26])([CH3:24])[CH3:25]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 2907754HCID 2907754, VerbindungHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 18727100HCID 18727100, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 8 (945 mg, 4.29 mmol), 1 (695 mg, 4.33 mmol), and acetic acid (1.31 g, 21.8 mmol) in methanol (10 mL) was treated with sodium cyanoborohydride (270 mg, 4.29 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium bicarbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. PCTLC (SiO2, 6 mm, 10% EtOH-90% CHCl3) afforded the title compound (9).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9e0bb2e2e06d4205bf7d78cf491df436
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376503B1

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