Sodium Glycinate → {[4-(4-Fluoro-benzyl)-1-hydroxy-3-oxo-6-trifluoromethyl-3,4-dihydro-4,4a-diaza-fluorene-2-carbonyl]-amino}-acetic acid

HRID 1512008Notes

Reaction equation

HRID 1512008 reaction equation
CO[C:3]([C:5]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:15]2[C:7](=[CH:8][C:9]3[C:14]2=[CH:13][C:12]([C:27]([F:30])([F:29])[F:28])=[CH:11][CH:10]=3)[C:6]=1[OH:31])=[O:4].[NH2:32][CH2:33][C:34]([O-:36])=[O:35].[Na+]>COCCO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:16]2[N:15]3[C:7](=[CH:8][C:9]4[C:14]3=[CH:13][C:12]([C:27]([F:28])([F:29])[F:30])=[CH:11][CH:10]=4)[C:6]([OH:31])=[C:5]([C:3]([NH:32][CH2:33][C:34]([OH:36])=[O:35])=[O:4])[C:17]2=[O:18])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4684308Sodium GlycinateHCID 687624054-(4-Fluoro-benzyl)-1-hydroxy-3-oxo-6-trifluoromethyl-3,4-dihydro-4,4a-diaza-fluorene-2-carboxylic acid methyl ester

Product 1

HCID 54751173{[4-(4-Fluoro-benzyl)-1-hydroxy-3-oxo-6-trifluoromethyl-3,4-dihydro-4,4a-diaza-fluorene-2-carbonyl]-amino}-acetic acidYield 56.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 4-(4-fluoro-benzyl)-1-hydroxy-3-oxo-6-trifluoromethyl-3,4-dihydro-4,4a-diaza-fluorene-2-carboxylic acid methyl ester (100 mg, 0.23 mmol) and sodium glycinate (224 mg, 2.3 mmol) in 2-methoxyethanol (3.3 mL) was microwaved at 150° C. for 1 h and concentrated. Residue was dissolved in water (80 mL) and acidified to pH=3-4 using 1 N HCl solution. Precipitate was collected and rinsed with water. Solid was then dissolved in EtOAc, dried over MgSO4, filtered and concentrated. Crude product was triturated in MeOH (3 mL) and solid was collected and dried in vacuo to provide the title compound 62 mg. ESI (m/z): 476.01 (M−H)−

Workup

  1. customwas microwaved at 150° C. for 1 h
  2. concentrationconcentrated
  3. dissolutionResidue was dissolved in water (80 mL)
  4. customPrecipitate was collected
  5. washrinsed with water
  6. dissolutionSolid was then dissolved in EtOAc
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customCrude product was triturated in MeOH (3 mL)
  11. customsolid was collected
  12. customdried in vacuo

Sources & evidence

ORD record
ord-b490fa418f75402db38091dc58b4c2e4
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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