Hydrochloric Acid → HCID 58078476, Verbindung

HRID 74774

Reaktionsgleichung

Reaktionsgleichung von HRID 74774
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@H:13]([O:19][CH3:20])[C@@H:14]([CH3:18])[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])(C)C.Cl.[CH:22]1[C:34]2C(COC(ON3C(=O)CCC3=O)=O)[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1.CO>O1CCOCC1.COCCOC>[CH:31]1[C:32]2[CH:4]([CH2:1][O:5][C:6]([N:8]3[CH2:12][CH2:11][CH2:10][C@H:9]3[C@H:13]([O:19][CH3:20])[C@@H:14]([CH3:18])[C:15]([OH:17])=[O:16])=[O:7])[C:34]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]=2[CH:28]=[CH:29][CH:30]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 11033491(2R,3R)-3-((2S)-1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid

Produkt 1

HCID 58078476HCID 58078476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a stirring solution of #11 (2.4 g, 8.4 mmol, 1.0 eq.) in 10 mL of dioxane under nitrogen, 4M HCl in dioxane (20 mL, 80 mM, 10 eq.) was added. The reaction was allowed to stir at room temperature for 3 hours before being concentrated in vacuo and placed underneath high vacuum. Crude material was then dissolved with 30 mL of 10% Na2CO3. This solution was then added to a stirring solution of 1-{[(9H-fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidine-2,5-dione (2.96 g, 8.77 mmol, 1.05 eq.) in 30 mL of DME. Reaction was allowed to stir at room temperature until TLC (20% methanol/40% ethyl acetate/40% heptanes) indicated the consumption of Boc de-protected starting material. The reaction was concentrated in vacuo to a smaller volume, washed twice with ether, acidified to pH 2 using concentrated HCl and then extracted three times with a solution of 90% dichloromethane 10% methanol. The organics where washed with saturated sodium bicarbonate and brine before being dried over sodium sulfate, filtered, and concentrated in vacuo to a brown solid #119 (3.4 g, quant.). LC-MS (Protocol Q): m/z 410.0 [M+H+], retention time=1.81 minutes.

Aufarbeitung

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionCrude material was then dissolved with 30 mL of 10% Na2CO3
  3. customReaction
  4. customthe consumption of Boc de-protected
  5. concentrationThe reaction was concentrated in vacuo to a smaller volume
  6. washwashed twice with ether
  7. extractionextracted three times with a solution of 90% dichloromethane 10% methanol
  8. washThe organics where washed with saturated sodium bicarbonate and brine
  9. dry with materialbefore being dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to a brown solid #119 (3.4 g, quant.)

Quellen und Nachweise

ORD-Eintrag
ord-df61c877757948e891bde0036fed85f9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828401B2

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