Water → HCID 22241639, compound

HRID 892009Notes

Reaction equation

HRID 892009 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[CH2:18][C:19]([OH:21])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O-:25])(=O)[CH3:23].[Na+].O.[C:28](OCC)(=O)C>C(OC(=O)C)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:22](=[O:25])[CH3:23])[N:13]=[C:12]2[CH2:18][C:19](=[O:21])[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 178525252HCID 178525252, compound

Product 1

HCID 22241639HCID 22241639, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (5-benzyloxy-1H-indazol-3-yl)-acetic acid (2 g, 7.08 mmol) and sodium acetate (0.99 g, 12 mmol) in acetic anhydride (6 ml) was stirred at 130° C. for 3 h. After cooling, water (15 ml) and ethyl acetate (15 ml) were added to the reaction mixture. The aqueous layer was separated and extracted with ethyl acetate (2×15 ml). The combined extracts were washed with saturated aqueous NaHCO3 (2×20 ml) and saturated aqueous NaCl (20 ml), dried (MgSO4), and evaporated to a residue which was purified by chromatography (silica, 15% ethyl acetate in hexane) to give a yellow solid (0.48 g): 1H NMR (CD3OD) δ 8.35–8.30 (m, 1H), 7.48–7.23 (m, 6H), 7.04–7.02 (m, 2H), 5.11 (s, 2H), 4.02 (s, 2H), 2.77 (s, 3H), 2.27 (s, 3H); 13C NMR (CDCl3)δ 203.64 (C), 170.47 (C), 156.20 (C), 145.04 (C), 136.52 (C), 128.64 (CH), 128.31 (CH), 127.60 (CH), 120.51 (CH), 116.74 (CH), 102.26 (CH), 70.68 (CH2), 42.76 (CH2), 29.59 (CH3), 22.77 (CH3), MS(APCl) m/z 323 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×15 ml)
  4. washThe combined extracts were washed with saturated aqueous NaHCO3 (2×20 ml) and saturated aqueous NaCl (20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residue which
  7. customwas purified by chromatography (silica, 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5ec0cd3b12b1465dbf4178abf5b8a1ef
Source dataset
uspto-grants-2006_02
Patent number
US07005443B1

Reaction notes

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