Lithium Hydroxide → 17-Ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acid

HRID 390117Notes

Reaction equation

HRID 390117 reaction equation
C([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[CH:13]1[CH:9]([CH2:10][CH:11]([O:26][CH2:27][O:28][CH2:29][CH3:30])[CH2:12]1)[C:8](=[O:31])[NH:7]2)=[O:5])C.C1COCC1.[Li+].[OH-]>CO>[CH2:29]([O:28][CH2:27][O:26][CH:11]1[CH2:10][CH:9]2[CH:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]3[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]2=[O:31])[CH2:23]3)[CH2:12]1)[CH3:30]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 6687123617-Ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acid ethyl ester

Product 1

HCID 6687157417-Ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acidYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester 1e (2.26 g) was mixed with THF (20 ml), MeOH (20 ml) and a solution of LiOH (1N 20, ml) and stirred at 55° C. for ˜17 h. The reaction mixture was concentrated by rotary evaporation, diluted with water (30-50 ml) and acidified with 10% citric acid to pH 3-4. The cloudy solution was extracted into ethyl acetate (3×50 ml). The combined organic extracts were washed with water and brine, and dried over magnesium sulfate. The drying agent was removed by filtration and the ethyl acetate was removed by rotary evaporation. The residue was dried on high vacuum which gave 2 g of the title compound as a white foam. The product was used directly without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. additiondiluted with water (30-50 ml)
  3. extractionThe cloudy solution was extracted into ethyl acetate (3×50 ml)
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe ethyl acetate was removed by rotary evaporation
  8. customThe residue was dried on high vacuum which

Sources & evidence

ORD record
ord-31d0be5f65004c3ca5212237fc776700
Source dataset
uspto-grants-2013_02
Patent number
US08383584B2

Reaction notes

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