StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Formaldehyde → HCID 86690385, Verbindung

HRID 513894
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 513894
[C:1]([O:4][C@@H:5]([C@:16]12[CH2:51][C:50](=[O:52])[C:49]([CH:53]([CH3:55])[CH3:54])=[C:17]1[C@@H:18]1[C@@:31]([CH3:34])([CH2:32][CH2:33]2)[C@@:30]2([CH3:35])[C@@H:21]([C@:22]3([CH3:48])[C@@H:27]([CH2:28][CH2:29]2)[C:26]([CH3:37])([CH3:36])[C@@H:25]([O:38][C:39](=[O:47])[CH2:40][C:41]([CH3:46])([CH3:45])[C:42]([OH:44])=[O:43])[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(=[O:3])[CH3:2].C=O.[BH3-][C:59]#N.[Na+]>CO>[C:1]([O:4][C@@H:5]([C@:16]12[CH2:51][C:50](=[O:52])[C:49]([CH:53]([CH3:55])[CH3:54])=[C:17]1[C@@H:18]1[C@@:31]([CH3:34])([CH2:32][CH2:33]2)[C@@:30]2([CH3:35])[C@@H:21]([C@:22]3([CH3:48])[C@@H:27]([CH2:28][CH2:29]2)[C:26]([CH3:37])([CH3:36])[C@@H:25]([O:38][C:39](=[O:47])[CH2:40][C:41]([CH3:45])([CH3:46])[C:42]([OH:44])=[O:43])[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[CH2:6][N:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[CH3:59])(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86690382HCID 86690382, Verbindung

Produkt 1

HCID 86690385HCID 86690385, VerbindungAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-1-acetoxy-2-((4-chlorobenzyl)amino)ethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (50) (150 mg, 0.192 mmol) in MeOH (6 mL) stirred in air at rt was added formaldehyde (31.2 mg, 0.384 mmol). The reaction mixture was stirred at rt for 2 h. Then it was added NaCNBH3 (85 mg, 1.345 mmol) portionwise and stirred for overnight. The solvent was evaporated and the residue diluted with DCM and washed with water and brine. The dried organics were filtered and concentrated to give 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-1-acetoxy-2-((4-chlorobenzyl)(methyl)amino)ethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (68) (120 mg, 65% yield) as a white solid. This material was used without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.31-7.26 (m, 2H), 7.24-7.16 (m, 2H), 5.65 (d, J=8.5 Hz, 1H), 4.50 (br. s., 1H), 3.66-3.51 (m, 1H), 3.49-3.36 (m, 1H), 3.27-3.06 (m, 2H), 2.73-2.32 (m, 5H), 2.26 (s, 3H), 2.08-0.73 (m, 49H); LC/MS: m/z calculated 793.5. found 794.3 (M+1)+.

Aufarbeitung

  1. stirringstirred for overnight
  2. customThe solvent was evaporated
  3. additionthe residue diluted with DCM
  4. washwashed with water and brine
  5. filtrationThe dried organics were filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1ffb928f64f044b0bda403b733b2029e
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102685B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion