Sodium Chloride → 3-{[2-(4-Methoxy-phenyl)-5,5-dimethyl-[1,3]dioxane-4-carbonyl]-amino}-propionic acid

HRID 12005

Reaktionsgleichung

Reaktionsgleichung von HRID 12005
[C:1]([OH:15])(=[O:14])[CH2:2][CH2:3][NH:4][C:5](=[O:13])[C@@H:6]([C:8]([CH2:11][OH:12])([CH3:10])[CH3:9])[OH:7].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.COO[CH:34](OOC)[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1.[Na+].[Cl-]>C(Cl)Cl>[CH3:42][O:41][C:38]1[CH:39]=[CH:40][C:35]([CH:34]2[O:7][CH:6]([C:5]([NH:4][CH2:3][CH2:2][C:1]([OH:15])=[O:14])=[O:13])[C:8]([CH3:10])([CH3:9])[CH2:11][O:12]2)=[CH:36][CH:37]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 6613Pantothenic AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 90893839p-Anisaldehyde-dimethoxy-acetal

Produkt 1

HCID 667537893-{[2-(4-Methoxy-phenyl)-5,5-dimethyl-[1,3]dioxane-4-carbonyl]-amino}-propionic acidAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pantothenic acid (7) (4.6 g, 2.24×10−2 mols) was dissolved in dry DCM (30 mL). Camphor sulfonic acid (0.52 g, 2.24×10−3 mols) and p-anisaldehyde-dimethoxy-acetal (3.82 mL, 2.24×10−2 mols) were added to the reaction mixture. The reaction was stirred overnight at room temperature with a drying tube. The crude reaction product was concentrated and purified silica gel chromatography (6:1 hexane:EtOAC-EtOAc) to yield a white solid (8A1) (3.8 g, 51% yield). mp=135-136° C. 1HNMR (400 MHz, DMSO) 0.93 (s, 3H), 0.99 (s, 3H), 2.38 (t, 2H, J=6.8 Hz), 3.25 (m, 1H), 3.34 (m, 1H), 3.5.9 (d, 1H, J=10.8 Hz), 3.62 (d, H, J=10.8 Hz), 3.74 (s, 3H), 4.07 (s, 1H), 5.50 (s, 1H), 6.91 (d, 2H, J=8.8 Hz), 7.41 (d, 2H, J=8.8 Hz). 13C-NMR (400 Mz, DMSO) 19.7, 22.2, 33.2, 34.4, 34.9, 55.8, 78.0, 83.8, 101.1, 114.0, 128.4, 131.1, 160.3, 168.9, 173.8. IR (NaCl, thin film), 3420, 2959, 1729, 1654, 1617, 1540, 1520, 1251, 1105 cm−1. MS (ESI) [M+Na]+360.1. HRMS (FAB) (m/z): [M+H]+ calcd for C17H23O6N, 338.1598, found 338.1594.

Aufarbeitung

  1. customThe crude reaction product
  2. concentrationwas concentrated
  3. custompurified silica gel chromatography (6:1 hexane:EtOAC-EtOAc)
  4. customto yield a white solid (8A1) (3.8 g, 51% yield)

Quellen und Nachweise

ORD-Eintrag
ord-aa18151d93744dfa8c50f3a6124f9344
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727738B2

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