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Triethylamine → (3beta,5beta,7alpha,12alpha)-3-(1-Oxopent-4-enyl)amino-7,12-dihydroxy-cholan-24-oic acid methyl ester

HRID 266024
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 266024
[C:1](O)(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:23][O:24][C:25](=[O:52])[CH2:26][CH2:27][C@H:28]([C@@H:30]1[C@:47]2([CH3:48])[C@H:33]([C@H:34]3[C@H:44]([CH2:45][C@@H:46]2[OH:49])[C@:42]2([CH3:43])[C@@H:37]([CH2:38][C@@H:39]([NH2:50])[CH2:40][CH2:41]2)[CH2:36][C@H:35]3[OH:51])[CH2:32][CH2:31]1)[CH3:29]>C1COCC1>[CH3:23][O:24][C:25](=[O:52])[CH2:26][CH2:27][C@H:28]([C@@H:30]1[C@:47]2([CH3:48])[C@H:33]([C@H:34]3[C@H:44]([CH2:45][C@@H:46]2[OH:49])[C@:42]2([CH3:43])[C@@H:37]([CH2:38][C@@H:39]([NH:50][C:1](=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:40][CH2:41]2)[CH2:36][C@H:35]3[OH:51])[CH2:32][CH2:31]1)[CH3:29]
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 611384-Pentenoic acidHCID 62365Isobutyl chloroformateHCID 10364902HCID 10364902, Verbindung

Produkt 1

HCID 54437505(3beta,5beta,7alpha,12alpha)-3-(1-Oxopent-4-enyl)amino-7,12-dihydroxy-cholan-24-oic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4-pentenoic acid (marketed product) and triethylamine in THF was added drop by drop, under nitrogen and at 5° C., to isobutyl chloroformate and subsequently with a solution of (3β,5β,7α,12α)-3-amino-7,12-dihydroxy-cholan-24-oic acid methyl ester (prepared according to the procedure described in EXAMPLE 5) in THF. When the reaction was over, solvent was evaporated and the residue was taken up with H2O and AcOEt. The organic phase was separated, washed with H2O, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by flash chromatography to obtain the desired product.

Aufarbeitung

  1. customwas evaporated
  2. customThe organic phase was separated
  3. washwashed with H2O
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-348cfa841ead497595c808489a63437d
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05649537

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