Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetate

HRID 469450

Reaktionsgleichung

Reaktionsgleichung von HRID 469450
[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[NH:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12])(=[O:3])[NH2:2].[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[C@@H:22](O)[CH2:21]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[NH:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([O:13][C@@H:22]1[CH:23]2[CH2:26][CH2:27][N:20]([CH2:25][CH2:24]2)[CH2:21]1)=[O:12])(=[O:3])[NH2:2]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 585569892-(2-Carbamoylthiophen-3-ylamino)-2-phenylacetic acid

Produkt 1

HCID 54763973(R)-quinuclidin-3-yl 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetateAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetic acid (I7) (389 mg, 1.41 mmol), (R)-quinuclidin-3-ol (215 mg, 1.69 mmol), DCC (349 mg, 1.69 mmol) and HOBT (259 mg, 1.69 mmol) in dry THF (5 ml) was stirred at room temperature overnight. THF was evaporated, and the crude product was taken up with EtOAc and washed twice with 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by preparative HPLC. The fractions with the product are combined and evaporated to dryness. The residue was dissolved in 2M K2CO3 and extracted twice with EtOAc to obtain (R)-quinuclidin-3-yl 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetate (32 mg, 6% yield).

Aufarbeitung

  1. customTHF was evaporated
  2. washwashed twice with 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by preparative HPLC
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in 2M K2CO3
  9. extractionextracted twice with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-ce04655f38de48979470b15eda76ccc0
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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