Triethylamine → (R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]benzenebutanoic acid allyl ester

HRID 1915

Reaktionsgleichung

Reaktionsgleichung von HRID 1915
[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.[C:24]([NH:34][C:35]([CH3:40])([C:37](O)=[O:38])[CH3:36])([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].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:37](=[O:38])[C:35]([NH:34][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])([CH3:40])[CH3:36])[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 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 22883347D-Homophenylalanine allyl ester

Produkt 1

HCID 67666530(R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]benzenebutanoic acid allyl esterAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The amine obtained in Step B of this Example (300 mg; 1.37 mmol) triethylamine (380 ml; 2.73 mmol) and N-carbobenzyloxy-2-methylalanine (278 mg; 1.37 mmol) were dissolved in dry methylene chloride (3 ml) and BOP (605 mg; 1.37 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and the resultant homogenous yellow solution quenched by addition of brine. The two phase system was extracted with methylene chloride (2×25 ml) and the combined methylene chloride layers dried over powdered anhydrous magnesium sulfate. Filtration of the methylene chloride solution to remove the spent drying agent followed by evaporation of solvent afforded an oil which was purified by column chromatography on silica gel using a solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant. The desired product (419 mg; 69.7%) was isolated as a white amorphous solid. FAB-MS:- calculated for C25 H30N2O5 438.2; found 439.3 (M+1).

Aufarbeitung

  1. customthe resultant homogenous yellow solution quenched by addition of brine
  2. extractionThe two phase system was extracted with methylene chloride (2×25 ml)
  3. dry with materialthe combined methylene chloride layers dried
  4. filtrationFiltration of the methylene chloride solution
  5. customto remove the
  6. customspent drying agent
  7. customfollowed by evaporation of solvent
  8. customafforded an oil which
  9. customwas purified by column chromatography on silica gel using
  10. additiona solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-2788899244b0487da69285b0cbf52602
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726319

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