Lithium hydroxide, monohydrate → 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid

HRID 423031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423031
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28]([O:30]CC)=[O:29])[CH2:18][CH2:17][N:16]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.C(O)C.CCOC(C)=O>[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28]([OH:30])=[O:29])[CH2:14][CH2:15][N:16]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:17][CH2:18]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Komponenten

7

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 57750296ethyl 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate2×

Produkt 1

HCID 446042214-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acidAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Lithium hydroxide monohydrate (0.556 g, 13.26 mmol) was added to ethyl 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate (Intermediate 11) (1.07 g, 2.65 mmol) in water (6.25 ml), THF (25 ml) and ethanol (25.00 ml). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). The aqueous was adjusted to pH5 with 1M citric acid solution then extracted with EtOAc (3×50 mL). The organic extracts were washed with saturated brine (25 mL) then dried over MgSO4, filtered and evaporated to afford desired product 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (0.628 g, 63.1%) as a white foam.

Aufarbeitung

  1. washwashed with water (20 mL)
  2. extractionthen extracted with EtOAc (3×50 mL)
  3. washThe organic extracts were washed with saturated brine (25 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-61da7afaeaaf4b2d9eafb3e4eca40de7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101623B2

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