Sodium Iodoacetate → 2-[[(4S,5R)-5-(1,2-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester

HRID 2078492Notes

Reaction equation

HRID 2078492 reaction equation
[OH:1][CH2:2][CH:3]1[CH:7]([CH:8]([OH:12])[CH:9]([OH:11])[CH3:10])[O:6][C:5]([CH3:14])([CH3:13])[O:4]1.I[CH2:16][C:17]([O-:19])=[O:18].[Na+].[OH-].[Na+].I[CH3:24]>O>[OH:12][CH:8]([C@H:7]1[O:6][C:5]([CH3:13])([CH3:14])[O:4][C@H:3]1[CH2:2][O:1][CH2:16][C:17]([O:19][CH3:24])=[O:18])[CH:9]([OH:11])[CH3:10]

Participants

6

Reactant 4

HCID 5239Sodium IodoacetateHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 226078864-(Hydroxymethyl)-5-(1,2-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 865887692-[[(4S,5R)-5-(1,2-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl esterYield 21.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 4-(hydroxymethyl)-5-(1,2-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolane (63 g, 0.33 mol) and sodium iodoacetate (75 g, 0.36 mol) in water was treated with solid sodium hydroxide (16 g, 0.35 mol). The reaction mixture was stirred overnight and then washed with ethyl acetate and ether. The aqueous layer was concentrated. The resulting residue was dissolved in DMF (20 mL) and treated with iodomethane (37 mL, 0.6 mol). The resulting reaction mixture was stirred overnight. The reaction mixture was diluted with two volumes of salt water and extracted with ethyl acetate (6×). The combined organic layers were dried, and concentrated to give 20 g of 2-[[(4S,5R)-5-(1,2-dihydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]ethanoic acid, methyl ester, a compound of formula (L), as a colorless viscous oil; 1H NMR (CDCl3) δ 1.27 (d, 3H), 1.38 (s, 3H), 1.48 (s, 3H), 3.57 (m, 1H), 3.77 (s, 3H), 3.8 (m, 2H), 4.13 (m, 2H), 4.4 (m, 2H) ppm.

Workup

  1. washwashed with ethyl acetate and ether
  2. concentrationThe aqueous layer was concentrated
  3. dissolutionThe resulting residue was dissolved in DMF (20 mL)
  4. customThe resulting reaction mixture
  5. stirringwas stirred overnight
  6. extractionextracted with ethyl acetate (6×)
  7. customThe combined organic layers were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bb359538bd60423f97ebf38493f0c803
Source dataset
uspto-grants-2011_04
Patent number
US07928255B2

Reaction notes

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