Citric Acid → HCID 66870865, Verbindung

HRID 1803717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803717
C([O:3][C:4]([C:6]12[CH2:24][CH:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:14](=[O:34])[N:13]1[CH:9]([CH2:10][CH:11]([O:35][C:36]3[C:45]4[C:40](=[C:41]([CH3:48])[C:42]([O:46][CH3:47])=[CH:43][CH:44]=4)[N:39]=[C:38]([C:49]4[S:50][CH:51]=[C:52]([CH:54]([CH3:56])[CH3:55])[N:53]=4)[CH:37]=3)[CH2:12]1)[C:8](=[O:57])[NH:7]2)=[O:5])C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[CH:54]([C:52]1[N:53]=[C:49]([C:38]2[CH:37]=[C:36]([O:35][CH:11]3[CH2:10][CH:9]4[N:13]([C:14](=[O:34])[N:15]([CH2:25][C:26]5[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=5)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH:23]5[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:57])[CH2:24]5)[CH2:12]3)[C:45]3[C:40](=[C:41]([CH3:48])[C:42]([O:46][CH3:47])=[CH:43][CH:44]=3)[N:39]=2)[S:50][CH:51]=1)([CH3:56])[CH3:55]

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 66870831HCID 66870831, Verbindung

Produkt 1

HCID 66870865HCID 66870865, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

Ethyl ester 137 (366 mg, 0.460 mmol) was dissolved in THF/MeOH/H2O 2:1:1 (30 mL) and 1M LiOH (4.6 mL, 4.40 mmol) was added dropwise at room temperature during 5 minutes after which the solution was stirred overnight. The mixture was acidified to pH 3-4 by addition of solid citric acid and the organic solvents were evaporated. The water phase was diluted with brine (50 mL) and was then extracted trice with DCM. The combined organic phase was washed twice with brine and was thereafter dried, filtered and concentrated. The crude was then purified by flash column chromatography (ethyl actetate/methanol 7:1) to give the title compound (212 mg, 60%). (M+H)+ calcd: 768.3; found: 768.7.

Aufarbeitung

  1. customthe organic solvents were evaporated
  2. additionThe water phase was diluted with brine (50 mL)
  3. extractionwas then extracted trice with DCM
  4. washThe combined organic phase was washed twice with brine
  5. customwas thereafter dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified by flash column chromatography (ethyl actetate/methanol 7:1)

Quellen und Nachweise

ORD-Eintrag
ord-9945cbc061014e9ba26ac2d71e875585
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349869B2

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