Water → HCID 67793156, compound

HRID 1034239Notes

Reaction equation

HRID 1034239 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C@H:13]1[C:17](=[O:18])[N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][C@H:14]1[C:25]([O:27]CC)=[O:26])=[O:11].[OH-].[Li+].O>CCO.C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C@@H:13]1[C:17](=[O:18])[N:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:15][C@H:14]1[C:25]([OH:27])=[O:26])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67793217HCID 67793217, compound

Product 1

HCID 67793156HCID 67793156, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To the ethyl ester of Example 4 (68 mg, 0.174 mmol) dissolved in 4:1 EtOH/THF was added an aqueous solution of lithium hydroxide (13 mg, 0.521 mmol). After stirring for 16 h at room temperature, 2.5 ml of water was added and the solution was extracted with chloroform. The aqueous layer was then acidified with 1N HCl to pH2 and extracted again with chloroform. The combined organic layers were dried over MgO4, filtered and concentrated in vacuo to give the crude acid which was chromatographed on silica gel eluting with 5/95/1 EtOH/CH2Cl2 /HOAc to give the title compound (27 mg, 42%) as a colorless powder. Anal calcd for C20H17N3O4 : C, 64.51; H, 4.87; N, 11.28. Found: C, 64.26; H, 4.62; N, 10.88. MS M+1 calcd for C20H17N3O4 364, found 364.

Workup

  1. extractionthe solution was extracted with chloroform
  2. extractionextracted again with chloroform
  3. customThe combined organic layers were dried over MgO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude acid which
  7. customwas chromatographed on silica gel eluting with 5/95/1 EtOH/CH2Cl2 /HOAc

Sources & evidence

ORD record
ord-18393f5b192947deba34e98b91ba5aea
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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