Triethylamine → [4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl ester

HRID 2121235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121235
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:5]=1)([O-:3])=[O:2].C1C=C2C(N(O)N=NC2=CC=1)=O.Cl.[CH3:33][O:34][C:35](=[O:42])[C@H:36]([CH2:38][CH2:39][S:40][CH3:41])[NH2:37].CCN=C=NCCCN(C)C.CCN(CC)CC>CN(C=O)C.C(OCC)(=O)C>[CH3:33][O:34][C:35](=[O:42])[C@H:36]([CH2:38][CH2:39][S:40][CH3:41])[NH:37][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 234360742-(2-Methylphenyl)-4-nitrobenzoic acid

Produkt 1

HCID 53719134[4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl esterAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product of Example 308A (604 mg, 2.35 mmol) and HOOBT (574 mg, 3.52 mmol) were dissolved in DMF (10 mL) and methionine methyl ester HCl (679 mg, 3.52 mmol) and EDCI (676 mg, 3.52 mmol) were added followed by Et3N (476 mg, 0.65 mL, 4.7 mmol). The reaction was stirred for 12 hours and then was taken up in ethyl acetate and washed successively with brine (3×) and water (3×). The ethyl acetate layer was dried over Na2SO4, filtered and evaporated. Purification by chromatography on silica gel (5% methanol-ethyl acetate) gave the desired compound (940 mg, 98%).

Aufarbeitung

  1. washwashed successively with brine (3×) and water (3×)
  2. dry with materialThe ethyl acetate layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography on silica gel (5% methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0aa2890e021e459dbc184aa991d60333
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693123B2

Notizen zur Reaktion

Wird geladen…