Dichloromethane → HCID 20737862, Verbindung

HRID 350333Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350333
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:7])([CH3:4])(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.C(Cl)(OCC1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2)=O>CCOCC>[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:22][CH:23]=1)([O:5][CH2:1][CH:4]1[C:43]2[C:44](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:45]2[C:50]1=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:7]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 343679-Fluorenylmethyl chloroformateHCID 69332259HCID 69332259, Verbindung

Produkt 1

HCID 20737862HCID 20737862, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To the above (S)-4-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxybenzoic acid was added CH2Cl2 (10 ml) and TFA (10 mL). The mixture was stirred at room temp for 1 hr Et2O was added to the mixture and resulting solid was collected. The solid was dissolved in water (100 mL), dioxane (50 mL) and NaHCO3 (4.4 g). Fmoc-Cl (3.34 g, 12.9 mmol) was added to the solution, and the resulting mixture was stirred for 20 hr at room temp. The mixture was washed with Et2O (×2) and aqueous layer was separated. The layer was acidified by the addition of 1 N HCl. The mixture was extracted with EtOAc. The extract was washed with water, brine, dried over MgSO4 and evaporated in vacuo to afford 5.36 g (91%) (S)-4-(1-Fmoc-2-pyrrolidinyl)methoxybenzoic acid as a viscous oil, which was crystallized on standing.

Aufarbeitung

  1. additionwas added to the mixture
  2. customresulting solid
  3. customwas collected
  4. dissolutionThe solid was dissolved in water (100 mL)
  5. washThe mixture was washed with Et2O (×2) and aqueous layer
  6. customwas separated
  7. additionThe layer was acidified by the addition of 1 N HCl
  8. extractionThe mixture was extracted with EtOAc
  9. washThe extract was washed with water, brine
  10. dry with materialdried over MgSO4
  11. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e9e0fca59cce46afbc1892dddb5e28dd
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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