Sodium Hydroxide → HCID 57750346, Verbindung

HRID 423081

Reaktionsgleichung

[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1([C:39]([O:41]C)=[O:40])[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[C:25]([CH:26]4[CH2:28][CH2:27]4)=[CH:24][N:23](S(C4C=CC(C)=CC=4)(=O)=O)[C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CCOC(C)=O>[C:3]([O:7][C:8]([NH:10][C:11]1([C:39]([OH:41])=[O:40])[CH2:12][CH2:13][N:14]([C:17]2[C:18]3[C:25]([CH:26]4[CH2:27][CH2:28]4)=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:15][CH2:16]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

2M sodium hydroxide solution (5.00 mL) was added to methyl 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate (Intermediate 63) (780 mg, 1.37 mmol) in THF (10 mL) at 20° C. The resulting solution was stirred at 40° C. for 24 hours. The reaction mixture was diluted with EtOAc (50 mL) and the aqueous layer was collected and acidified to pH4 with 2M HCl solution. The aqueous layer was extracted with DCM (2×50 mL) and the organic layers combined and washed with saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (375 mg, 68.2%) as a cream solid.

Aufarbeitung

customthe aqueous layer was collected
extractionThe aqueous layer was extracted with DCM (2×50 mL)
washwashed with saturated brine (50 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-a11ccb64ed894fcd90c8962c38b2578b
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101623B2

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