Tetrahydrofuran → HCID 68297182, compound

HRID 919849Notes

Reaction equation

HRID 919849 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([OH:35])=[C:13]2[C:18](=[CH:19][N:20]=1)[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16](=[O:28])[C:15]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:14]2)=[O:10])C.[OH-].[Na+].C1COCC1>CO>[CH2:21]([N:17]1[C:18]2[C:13](=[C:12]([OH:35])[C:11]([C:9]([NH:8][CH2:7][CH2:6][CH2:5][C:4]([OH:36])=[O:3])=[O:10])=[N:20][CH:19]=2)[CH:14]=[C:15]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:16]1=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68297359HCID 68297359, compound

Product 1

HCID 68297182HCID 68297182, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[(1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]-butyric acid ethyl ester (38 mg, 0.078 mmol), 2M aq. NaOH (4 mL), THF (4 mL) and MeOH (4 mL) was stirred at r.t. for 16 h. Solvent was evaporated in vacuo to one-third of its original volume, and the mixture was placed in an ice bath. 1 M HCl was added until pH about 2, and the resulting precipitate was collected by filtration and dried to give 27 mg of the title compound as a pale yellow solid. MS: (+) m/z 458.36 (M+1).

Workup

  1. customSolvent was evaporated in vacuo to one-third of its original volume
  2. customthe mixture was placed in an ice bath
  3. addition1 M HCl was added until pH about 2
  4. filtrationthe resulting precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-a912db34d77348a9a6be083a037afac5
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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