Sodium Hydroxide → HCID 86754478, compound

HRID 618153Notes

Reaction equation

HRID 618153 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][N:6]([C:10](=[O:28])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]=1[NH2:27])[CH:7]1[CH2:9][CH2:8]1)C.[OH-].[Na+]>CO>[C:20]([C:16]1[C:15]([NH2:27])=[C:14]([CH2:13][CH2:12][CH2:11][C:10]([N:6]([CH:7]2[CH2:9][CH2:8]2)[CH2:5][C:4]([OH:29])=[O:3])=[O:28])[CH:19]=[CH:18][N:17]=1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70070296HCID 70070296, compound

Product 1

HCID 86754478HCID 86754478, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ester 7-3 (1.07 g, 2.64 mmol) was dissolved in 26 mL MeOH, then treated with 1 N NaOH (6.6 mL, 6.6 mmol). After stirring overnight the reaction was concentrated, redissolved in water, the pH was adjusted to 1 with 10% KHSO4, then extracted with EtOAc (5×). The aqueous phase was adjusted to pH 3 with aq. NaOH, then reextracted with EtOAc (2×). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated, providing 7-4 as a white foam.

Workup

  1. concentrationwas concentrated
  2. dissolutionredissolved in water
  3. extractionextracted with EtOAc (5×)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4bdcdc813cd44f5e97fb375d69afb540
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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