Water → HCID 57971679, compound

HRID 2360640Notes

Reaction equation

HRID 2360640 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:20])[NH:11][O:12][CH:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:14].O.[OH-].[Li+]>C1COCC1>[CH2:16]([O:15][CH:13]([O:12][NH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[O:20])[CH3:14])[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57971668HCID 57971668, compound

Product 1

HCID 57971679HCID 57971679, compoundYield 828.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(1-Isobutoxy-ethoxycarbamoyl)-heptanoic acid methyl ester (36.6 g, 12.1 mmol, 1.0 eq) was stirred in THF (200 mL) and water (200 mL) in the presence of lithium hydroxide (8.68 g, 36.2 mmol, 3.0 eq) for 3 h at 50° C. THF was evaporated under vacuum and to the mixture water (100 mL) and ethyl acetate (200 mL) were added. The mixture was acidified cautiously to pH 3 by addition of 1N HCl. The organic phase was isolated and the aqueous layer re-extracted with ethyl acetate (150 mL). The organic phases were combined, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (29.0 g, 83% yield), m/z 288 [M++H]+ and used in stage 4 without further purification.

Workup

  1. customTHF was evaporated under vacuum and to the mixture water (100 mL) and ethyl acetate (200 mL)
  2. additionwere added
  3. additionThe mixture was acidified cautiously to pH 3 by addition of 1N HCl
  4. customThe organic phase was isolated
  5. extractionthe aqueous layer re-extracted with ethyl acetate (150 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e538419f55142a581f2c37b610399f1
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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