1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-{4-[(2,2-di-methyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-di-benzylbutyryl}-(L)-homophenylalanine

HRID 374321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 374321
[CH2:1]([C@H:8]([CH2:25][C@@H:26](CC1C=CC=CC=1)[C:27](O)=O)[C:9]([NH:11][C@H:12]([C:22]([OH:24])=[O:23])[CH2:13]OCC1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:37][C:38]1([CH3:67])[O:42][CH:41]([CH2:43][O:44][C:45]([C@H](CC2C=CC=CC=2)C[C@@H](CC2C=CC=CC=2)C(O)=O)=[O:46])[CH2:40][O:39]1.Cl.CN(C)[CH2:71][CH2:72][CH2:73]N=C=NCC>C(OCC)(=O)C>[CH3:37][C:38]1([CH3:67])[O:42][CH:41]([CH2:43][O:44][C:45]([C@H:26]([CH2:27][C:71]2[CH:72]=[CH:73][CH:25]=[CH:8][CH:9]=2)[CH2:25][C@@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]([NH:11][C@H:12]([C:22]([OH:24])=[O:23])[CH2:13][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[O:46])[CH2:40][O:39]1

Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14557690N-[(S,S)-2,4-dibenzyl-4-carboxybutyryl]-O-benzyl-(L)-serineHCID 149971524-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid

Produkt 1

HCID 86744820N-{4-[(2,2-di-methyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-di-benzylbutyryl}-(L)-homophenylalanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.5 g of (L)-homophenylalanine 1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yl ester, 0.51 g of 4-[(2,2-dimethyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-dibenzylbutyric acid is added 0.23 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The solution is stirred overnight. The solution is diluted with ethyl acetate, washed in sequence with 1N hydrochloric acid, water, saturated sodium bicarbonate, water, dried (Na2SO4), filtered and concentrated. The residue is flash chromatographed on silica gel eluting with ethyl acetate-methylene chloride (1:4) giving N-{4-[(2,2-di-methyl-1,3-dioxolan-4-yl)-methoxycarbonyl]-(S,S)-2,4-di-benzylbutyryl}-(L)-homophenylalanine 1,2:5,6-di-O-iso-propylidene-D-glucofuranos-3-yl ester melting at 48°-50°.

Aufarbeitung

  1. washwashed in sequence with 1N hydrochloric acid, water, saturated sodium bicarbonate, water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel eluting with ethyl acetate-methylene chloride (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-ea2d79ac971a4e73a55d0628bbe9e21b
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166212

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