Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(4-chlorophenylamino)-2-phenylacetate

HRID 1044041

Reaktionsgleichung

Reaktionsgleichung von HRID 1044041
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46](O)[CH2:45]2>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:10]([O:12][C@@H:46]2[CH:47]3[CH2:50][CH2:51][N:44]([CH2:49][CH2:48]3)[CH2:45]2)=[O:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 305145(4-Chloro-phenylamino)-phenyl-acetic acid

Produkt 1

HCID 46840420(R)-quinuclidin-3-yl 2-(4-chlorophenylamino)-2-phenylacetateAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-chlorophenylamino)-2-phenylacetic acid (I11) (574 mg, 2.20 mmol) in dry THF (20 ml), were added DCC (543 mg, 2.64 mmol), HOBt (359 mg, 2.64 mmol), and 3(R)-quinuclidinol (558 mg, 4.40 mmol). The resulting mixture was stirred at RT overnight (UPLC-MS monitoring: complete conversion). The solvent was evaporated, and the residue was partitioned between EtOAc and 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The resulting crude was purified by flash chromatography (DCM/MeOH=99/1 to 85/15) to obtain the title compound (306 mg, 37% yield, mixture of diastereomers).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between EtOAc and 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting crude was purified by flash chromatography (DCM/MeOH=99/1 to 85/15)

Quellen und Nachweise

ORD-Eintrag
ord-73fcd8624b4848568cea578149a9d504
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563577B2

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