Diisopropylethylamine → Morpholine-4-carboxylic acid[(r)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide

HRID 460410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460410
[NH2:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][CH2:4][CH:3]1[OH:9].C(N(C(C)C)CC)(C)C.[N:19]1([C:25]([NH:27][C@@H:28]([CH2:32][S:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:35])=[O:34])[C:29](O)=[O:30])=[O:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[OH:9][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH:2]1[NH:1][C:29]([C@@H:28]([NH:27][C:25]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:26])[CH2:32][S:33]([CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)(=[O:35])=[O:34])=[O:30]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 3196702-Aminocyclohexane-1,3-diolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11439693(R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid

Produkt 1

HCID 86612924Morpholine-4-carboxylic acid[(r)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amideAusbeute 10,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-amino-cyclohexane-1,3-diol (0.55 g) in dimethylformamide (30 ml) was treated with diisopropylethylamine (1.6 ml, 9.2 mmol). After stirring at room temperature for 5 minutes the mixture was treated with (R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (1.73 g, 4.86 mmol) followed by HATU (1.68 g, 4.42 mmol). This mixture was stirred at room temperature overnight and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate and then a mixture of ethyl acetate and methanol to give morpholine-4-carboxylic acid [(R)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide as a white solid (210 mg). MS: 470 (MH+).

Aufarbeitung

  1. stirringThis mixture was stirred at room temperature overnight
  2. customevaporated
  3. additiona mixture of ethyl acetate and methanol

Quellen und Nachweise

ORD-Eintrag
ord-82b8d578b0014890a5bb0029e1078d47
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196099B2

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