Bicarbonate Ion → 2-[(2,4-Diamino-pteridin-6-ylmethyl)-amino]-3-(4-hydroxy-phenyl)-propionic Acid Tert-butyl Ester

HRID 1272480

Reaktionsgleichung

Br.Br[CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15].[C:16]([O:20][C:21](=[O:32])[CH:22]([NH2:31])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)([CH3:19])([CH3:18])[CH3:17].C(=O)(O)[O-]>CN(C)C(=O)C>[C:16]([O:20][C:21](=[O:32])[CH:22]([NH:31][CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)([CH3:19])([CH3:17])[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (31.2 mg, 0.116 mmol) in anhydrous N,N dimethylacetamide was added 2-amino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester (30.22 mg, 0.127 mmol). The reaction mixture was stirred at 50° C. overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 17.2 mg product was obtained. Yield: 71%; 1H NMR (500 MHz, DMSO-d6): δ 1.33577 (s, 9H), 2.94185–3.02295 (m, 2H), 3.6550(b, 1H), 4.0878 (s, 2H), 6.70174–6.72384 (dd, J1=8.545 Hz, J2=2.59 Hz, 2H), 7.02394–7.04103 (d, J=8.545 Hz, 2H); 9.38501 (s, 1H); ESI-MS: 412 (M++1)

Aufarbeitung

customThe resulted precipitate was collected
custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-db528565b4e64ba28567f89edb9fd6e7
Quelldatensatz: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07208493B2

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