Triethylamine → (R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl ester

HRID 1919

Reaktionsgleichung

Reaktionsgleichung von HRID 1919
[CH2:1]([O:4][C:5](=[O:18])[C@@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[NH2:7])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH2:26]([O:33][C:34]([NH:36][C:37]([CH3:42])([C:39](O)=[O:40])[CH3:38])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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.C(OCC)(=O)C>[CH2:26]([O:33][C:34]([NH:36][C:37]([CH3:42])([CH3:38])[C:39]([NH:7][C@H:6]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:18])=[O:40])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 7006689D-Tryptophan allyl ester

Produkt 1

HCID 86752262(R)-alpha-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl esterAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenched with saturated brine (5 ml). The methylene chloride layer was separated, dried with magnesium sulfate and filtered then the volatiles removed under reduced pressure to leave a dark brown oil. Chromatography of this oil on silica gel using ethyl acetate and hexanes 2:1 v/v afforded 322 mg (84.5%) of the desired product. FAB-MS:- calculated for C26H29N3O5 463.2; found 464.5 (M+1).

Aufarbeitung

  1. customthe reaction quenched with saturated brine (5 ml)
  2. customThe methylene chloride layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed under reduced pressure
  6. customto leave a dark brown oil

Quellen und Nachweise

ORD-Eintrag
ord-275c3bd4a2eb43f196b2a4707e52cd1b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726319

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