Dicyclohexylcarbodiimide → Benzyl N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]carbamate

HRID 129718

Reaktionsgleichung

Reaktionsgleichung von HRID 129718
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10](O)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O[N:24]1C(=O)CC[C:25]1=O.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:24][CH3:25])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 80170N-Hydroxysuccinimide

Produkt 1

HCID 13443905Benzyl N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]carbamateAusbeute 107,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1.00 g of Cbz-Phe-OH (Sigma Chemical Company), 0.385 g of N-hydroxysuccinimide and 0.541 g of 1,3-dicyclohexylcarbodiimide in 5 mL of dry THF was kept at 4° C. under N2 overnight. The resulting precipitate was removed by filtration, and to the filtrate was added excess 40% aqueous methylamine at room temperature. The mixture was stirred at room temperature for 30 min. The solid was removed by filtration and the filtrate was partitioned between saturated aqueous NaHCO3 and CH2Cl2. The organic layer was separated, dried over anhydrous Na2SO4, and evaporated under reduced pressure to give 1.12 g of the crude Cbz-Phe-NHMe.

Aufarbeitung

  1. customThe resulting precipitate was removed by filtration
  2. additionto the filtrate was added excess 40% aqueous methylamine at room temperature
  3. customThe solid was removed by filtration
  4. customthe filtrate was partitioned between saturated aqueous NaHCO3 and CH2Cl2
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a1374cc68e8a4265af61199157d2232f
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470834

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