Triethylamine → (R)-alpha-[(4-Benzyloxycarbonylamino-4-methyl-1-oxopentyl)amino]benzenebutanoic acid allyl ester

HRID 1917

Reaktionsgleichung

Reaktionsgleichung von HRID 1917
[CH2:1]([O:4][C:5](=[O:16])[C@@H:6]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:7])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH2:24]([O:31][C:32]([NH:34][C:35]([CH3:42])([CH3:41])[CH2:36][CH2:37][C:38](O)=[O:39])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH2:1]([O:4][C:5](=[O:16])[C@H:6]([NH:7][C:38](=[O:39])[CH2:37][CH2:36][C:35]([NH:34][C:32]([O:31][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:33])([CH3:42])[CH3:41])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 196927754-(Benzyloxycarbonylamino)-4-methylpentanoic acidHCID 22883347D-Homophenylalanine allyl ester

Produkt 1

HCID 67666889(R)-alpha-[(4-Benzyloxycarbonylamino-4-methyl-1-oxopentyl)amino]benzenebutanoic acid allyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

D-Homophenylalanine allyl ester (175 mg; 0.80 mmol) (see Example 9, Step B), triethylamine (222 μl; 1.59 mmol) were dissolved in dry methylene chloride (2 ml) and 4-(benzyloxycarbonylamino)-4-methyl-pentanoic acid (211 mg; 0.80 mmol) added. The solution was stirred at room temperature and BOP (353 mg; 0.80 mmol) was added over 5 minutes, and this reaction mixture stirred at room temperature for 17 h. The reaction was quenched by adding brine and then the products of the reaction isolated by extraction with methylene chloride (3×15 ml). The methylene chloride layers were combined and dried with anhydrous magnesium sulfate powder, filtered and evaporated under reduced pressure. A thick golden yellow gum was obtained which was purified by column chromatography on silica gel using ethyl acetate and hexanes 1:2 v/v. The product (182 mg; 48.9%) was isolated as a pale yellow gum. FAB-MS:- calculated for C27H34 N2O5 466.3; found 467.7 (M+1).

Aufarbeitung

  1. stirringthis reaction mixture stirred at room temperature for 17 h
  2. customThe reaction was quenched
  3. additionby adding brine
  4. customthe products of the reaction isolated by extraction with methylene chloride (3×15 ml)
  5. dry with materialdried with anhydrous magnesium sulfate powder
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customA thick golden yellow gum was obtained which
  9. customwas purified by column chromatography on silica gel
  10. customThe product (182 mg; 48.9%) was isolated as a pale yellow gum

Quellen und Nachweise

ORD-Eintrag
ord-82c7b29aec314de1861faac34ed15227
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726319

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