Sodium Acetate → HCID 68618323, compound

HRID 2405855Notes

Reaction equation

HRID 2405855 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:13](=[O:32])[N:12]1[CH:8]([CH2:9][CH:10]([O:33][C:34]([N:36]3[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][C:42]=4[F:45])[CH2:37]3)=[O:35])[CH2:11]1)[C:7](=[O:46])[NH:6]2)=[O:4].C([O-])(=O)C.[Na+]>COCCOC.O>[CH3:1][O:2][C:3]([C:5]12[CH2:23][CH:22]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[C:13](=[O:32])[N:12]1[CH:8]([CH2:9][CH:10]([O:33][C:34]([N:36]3[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][C:42]=4[F:45])[CH2:37]3)=[O:35])[CH2:11]1)[C:7](=[O:46])[NH:6]2)=[O:4]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 68615924HCID 68615924, compound

Product 1

HCID 68618323HCID 68618323, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

To 14-tert-butoxycarbonylamino-18-(4-fluoro-1,3-dihydro-isoindole-2-carbonyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid methyl ester (392 mg, 0.61) in DME (3 mL) and water (1 mL) was added tosyl hydrazide (682 mg, 3.66 mmol) and sodium acetate (600 mg, 7.32 mmol). The reaction was heated to 95° C. and allowed to stir 1 hour. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography on silica (40→60% EtOAc/Hexanes) to provide 14-tert-butoxycarbonylamino-18-(4-fluoro-1,3-dihydro-isoindole-2-carbonyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadecane-4-carboxylic acid methyl ester (319 mg, 81% yield). LCMS found 644.8 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography on silica (40→60% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-4b8c6870110149309f57970eeb07003d
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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