Benzoyl chloride → 2,6-di-(N-benzoyl)amino-3-hydroxyheptanedioic acid, diethyl ester

HRID 568967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568967
[NH2:1][CH:2]([CH:8]([OH:26])[CH2:9][CH2:10][CH:11]([NH:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(CC)CC.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[C:34]([NH:1][CH:2]([CH:8]([OH:26])[CH2:9][CH2:10][CH:11]([NH:17][C:18](=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 140975952-amino-3-hydroxy-6-(N-benzoyl)aminoheptanedioic acid, diethyl ester

Produkt 1

HCID 140975962,6-di-(N-benzoyl)amino-3-hydroxyheptanedioic acid, diethyl esterAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Amine (9) (4.0 g, 10.9 mM) is taken up in CH2Cl2 (150 ml), cooled in an ice bath, and treated with Et3N (1.67 ml, 12 mM). Benzoyl chloride (1.27 ml, 10.9 mM) is added slowly over a period of 5 minutes and stirring continued at 4° C. for 1 hour. The reaction is warmed to room temperature and stirred overnight. This mixture is washed with 5% aqueous HCl (3×100 ml), saturated aqueous NaCl (3×100 ml), dried over anhydrous MgSO4, filtered and evaporated to dryness in vacuo to yield a white foam. The latter is purified by flash chromatography on silica gel eluting with 12% acetone/CH2Cl2 to yield 3.0 g (59% yield) of the desired product as a white foam. 'H-N.M.R. (CDCl3 /TMS): δ=1.19 (t, 3H, --CH2CH3); 1.22 (t, 3H, --CH2CH3); 1.40-2.27 (m, 4H, --CH2CH2 --); 4.19 (2q, 4H, --CH2CH3); 4.00-5.00 (4H, 10H, 2>CHCO2Et, CHOH); 6.90-7.86 ppm (m, 12H, 2NH and 2Ph).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. stirringstirred overnight
  3. washThis mixture is washed with 5% aqueous HCl (3×100 ml), saturated aqueous NaCl (3×100 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customto yield a white foam
  8. customThe latter is purified by flash chromatography on silica gel eluting with 12% acetone/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-8c41092dd00b4ab8a6ee5684b6a32cc4
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04730006

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