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

HRID 12005

Reaction equation

HRID 12005 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-aa18151d93744dfa8c50f3a6124f9344
Source dataset
uspto-grants-2010_06
Patent number
US07727738B2

Linked notes

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