Hydrochloric Acid → HCID 68492618, compound

HRID 1443701Notes

Reaction equation

HRID 1443701 reaction equation
O[Li].O.C[O:5][C:6](=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[N:15]=1.Cl>O.O1CCOCC1>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[N:15]=[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:24])=[O:5])[S:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59167790HCID 59167790, compound

Product 1

HCID 68492618HCID 68492618, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add a solution of LiOH.H2O (2.62 g, 62.5 mmol) in water (60 mL) to a rapidly stirred solution of 5-[4-(2-methoxy-phenyl)-thiazol-2-yl]-pentanoic acid methyl ester (3.82 g, 12.5 mmol) in dioxane (120 mL), stir at room temperature. After 1 hour, acidify to pH 1 with 5N HCl solution and concentrate to remove the majority of the dioxane. Partition residue between 20% i-PrOH/CHCl3 and 1N HCl solution, separate layers. Backextract from aqueous layer with 20% i-PrOH/CHCl3 and dry combined organic layers over MgSO4, and concentrate to get 3 grams of a pink oil. Recrystallize from EtOAc to afford the title compound (2.52 g, 69%). MS (IS) 292 (M+1)+.

Workup

  1. concentrationconcentrate
  2. customto remove the majority of the dioxane
  3. customPartition residue between 20% i-PrOH/CHCl3 and 1N HCl solution, separate layers
  4. dry with materialBackextract from aqueous layer with 20% i-PrOH/CHCl3 and dry
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-c5461bcec23e478a96f77f111f524fc1
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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