Acetic Acid → HCID 69732875, Verbindung

HRID 2416425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2416425
[CH2:1]([N:8]1[C:13]2[N:14]([CH3:27])[C:15](=[O:26])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([OH:25])[CH3:24])[C:17](=[O:18])[C:12]=2[C:11](=[O:28])[CH:10]=[C:9]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49](O)(=[O:51])[CH3:50].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:49]([O:25][C@@H:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][N:16]1[C:17](=[O:18])[C:12]2[C:11](=[O:28])[CH:10]=[C:9]([CH3:29])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:13]=2[N:14]([CH3:27])[C:15]1=[O:26])(=[O:51])[CH3:50]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 60123474HCID 60123474, Verbindung

Produkt 1

HCID 69732875HCID 69732875, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of (R)-8-benzyl-1,7-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.26 g, 3.18 mmol), triphenylphosphine (2.50 g, 9.52 mmol), acetic acid (0.54 ml, 9.52 mmol) and tetrahydrofuran (20 ml), cooled in an ice bath, was added diethylazodicarboxylate (1.5 ml, 9.5 mmol) dropwise. After stirring at room temperature for 4hours, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-hexanes to afford (S)-3-(5-acetoxyhexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.2 g, 86% yield) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.20 (d, 3H), 1.30-1.75 (m, 6H), 2.02 (s, 3H), 2.49 (s, 3H), 3.67 (s, 3H), 4.03 (t, 2H), 4.88 (sextet, 1H), 5.30 (s, 2H), 6.56 (s, 1H), 7.30-7.56 (m, 5H).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-283ccd95c09246eda992ed412020edda
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825180B2

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