4-Methylmorpholine → N-tert.-butoxycarbonyl-beta-alanyl-L-proline amide

HRID 1263304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1263304
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH2:19])=[O:18].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([N:15]1[CH2:22][CH2:21][CH2:20][C@H:16]1[C:17]([NH2:19])=[O:18])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 12707183(S)-Pyrrolidine-2-carboxamide monohydrochloride

Produkt 1

HCID 22826873N-tert.-butoxycarbonyl-beta-alanyl-L-proline amideAusbeute 33,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6.28 g (0.0332 m) of N-tert.-butoxycarbonyl-β-alanine, 5.0 g (0.0332 m) of L-proline amide hydrochloride, 8.96 g (0.0664 m) of 1-hydroxybenzotriazole, 12 ml of N-methylmorpholine, 75 ml of tetrahydrofuran, 40 ml of dimethylformamide and 6.84 g (0.0332 m) of dicyclohexylcarbodiimide was stirred at 25° for 17 hours. The solvents were evaporated in vacuo and the residue dissolved in ethyl acetate and water. The separated organic layer was washed with small volumes of dilute hydrochloric acid, brine, 5% bicarbonate and brine. The dried extract was concentrated to give 3.2 g of syrupy N-tert.-butoxycarbonyl-β-alanyl-L-proline amide. The methane chemical ionization mass spectrum was in agreement with the dipeptide structure.

Aufarbeitung

  1. customThe solvents were evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe separated organic layer was washed with small volumes of dilute hydrochloric acid, brine, 5% bicarbonate and brine
  4. extractionThe dried extract
  5. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-697f7490826e4b24bbf43388f926f328
Quelldatensatz
uspto-grants-1984_06
Patentnummer
US04456594

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