HCID 76674923, compound → HCID 21619023, compound

HRID 1733420Notes

Reaction equation

HRID 1733420 reaction equation
[C:1]([NH:8][CH:9]([C:17]([CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CC(C)=O.[OH-].[Na+].O>[C:1]([NH:8][CH:9]([C:17]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 1

HCID 76674923HCID 76674923, compound

Product 1

HCID 21619023HCID 21619023, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of the keto-ester (5) (16.0 mg, 0.046 mmoles) in acetone (0.39 ml) and sodium hydroxide (0.118 M, 0.39 mls) is stirred at room temperature for 2.0 hours. The solution is diluted with water and extracted once with ethyl acetate. The aqueous phase is acidified to pH 3 with citric acid and extracted thrice with ethyl acetate. The ethyl acetate is washed with water and saline and dried over magnesium sulphate. Evaporation of the solvent affords the pure keto-acid (6). (14.7 mg, 100%) as a colourless gum. νmax (CHCl3): 1710, 1490 cm-1. τ(CHCl3): 2.8 (5H, multiplet, C6H5), ca 3.6 broad (D2O-exchangeable, COOH), 4.95 (1H multiplet, D2O-exchangeable, NH), 5.66 (1H, multiplet, CH), 6.86-7.65 (6H, complex, 3×CH2), 8.62 (9H, s, BOC--tBu).

Workup

  1. extractionextracted once with ethyl acetate
  2. extractionextracted thrice with ethyl acetate
  3. washThe ethyl acetate is washed with water and saline
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-153501d1013a41e88beef87a5ee42630
Source dataset
uspto-grants-1980_12
Patent number
US04242256

Reaction notes

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