L-Methionine → tert-Butyl N-[(benzyloxy)carbonyl]-L-methionyl-L-alaninate

HRID 7272

Reaktionsgleichung

Reaktionsgleichung von HRID 7272
[NH2:1][C@H:2]([C:7]([OH:9])=O)[CH2:3][CH2:4][S:5][CH3:6].Cl.CN(C)CCCN=C=NCC.[CH:22]1[CH:23]=[CH:24][C:25]2N(O)N=N[C:26]=2[CH:27]=1.[C:32]([O:36][C:37](=[O:41])[C@H:38]([CH3:40])[NH2:39])([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C.C(N(CC)CC)C>[CH2:32]([O:36][C:37]([NH:1][C@H:2]([C:7]([NH:39][C@H:38]([C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:41])[CH3:40])=[O:9])[CH2:3][CH2:4][S:5][CH3:6])=[O:41])[C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:27]=1

Komponenten

7

Edukt 4

HCID 6137L-MethionineHCID 757711-HydroxybenzotriazoleHCID 89016L-Alanine 1,1-dimethylethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 16124765tert-Butyl N-[(benzyloxy)carbonyl]-L-methionyl-L-alaninateAusbeute 109,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Z-Protected L-methionine (10 g) was dissolved in DMF (200 ml) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (8.13 g) was added followed by HOBT (5.72 g) and triethylamine (19.7 ml). The mixture was stirred for 1 h then L-alanine tert-butyl ester (7.7 g) was added and stirring continued for 18 h. The mixture was concentrated under reduced pressure and partitioned between diethyl ether and water. The separated organic phase was washed with hydrochloric acid (1M), saturated sodium bicarbonate solution and brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (11.9 g) as an orange oil which crystallised on standing.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 18 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompartitioned between diethyl ether and water
  5. washThe separated organic phase was washed with hydrochloric acid (1M), saturated sodium bicarbonate solution and brine
  6. dry with materialdried (over magnesium sulphate)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-acb43fa5eb1b42d09e33b5d59c24f091
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084139B2

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