Lithium Hydroxide → 2-(6-Bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid

HRID 538303Notes

Reaction equation

HRID 538303 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:25])[C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=1)([CH2:13][O:14][CH2:15][O:16][CH3:17])[CH2:8][O:9][CH2:10][O:11][CH3:12])C>C(O)C.O>[Br:24][C:20]1[N:19]=[C:18]([C:7]([CH2:8][O:9][CH2:10][O:11][CH3:12])([CH2:13][O:14][CH2:15][O:16][CH3:17])[C:6]([OH:25])=[O:5])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 866680172-(6-Bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid ethyl ester

Product 1

HCID 866680182-(6-Bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (10.69 g, 254.95 mmol) was added to a solution of 2-(6-bromo-pyridin-2-yl)-3-methoxymethoxy-2-methoxymethoxymethyl-propionic acid ethyl ester (20.0 g, 50.99 mmol) in ethanol (100 ml) and water (100 ml) at rt and the reaction mixture was allowed to stir overnight. The reaction mass was concentrated under reduced pressure and acidified with dilute HCl and at 0° C. The product was extracted with ethyl acetate, washed with minimum amount of brine. Organic layer was concentrated under reduced pressure to obtain title compound as a brown liquid. Yield=18.0 g. TLC (50% ethyl acetate in hexane) Rf=0.05; LCMS: RtH8=1.383, [M+1]=364.0 and 366.0; HPLC: RtH9=3.844 min (49%) and 3.885 min. (22%).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customacidified with dilute HCl and at 0° C
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with minimum amount of brine
  5. concentrationOrganic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc67710063254f578977a61fdfeb9928
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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