Oxalic Acid → HCID 19045416, compound

HRID 1781367Notes

Reaction equation

HRID 1781367 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C:3]2([CH2:11][C:10](=[O:12])[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[O:7]2)[CH2:2]1.S(O[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:26][CH:25]=1)(=O)(=O)C.C(=O)(O)[O-].[Na+].[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42]>C(O)C>[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42].[CH3:34][S:31]([NH:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][N:1]2[CH2:6][CH2:5][CH2:4][C:3]3([CH2:11][C:10](=[O:12])[C:9]4[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=4[O:7]3)[CH2:2]2)=[CH:25][CH:26]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 516892Sodium Bicarbonate2×HCID 149859624-Methanesulphonamidophenethyl mesylateHCID 19045429HCID 19045429, compound

Product 1

HCID 19045416HCID 19045416, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 560 mg (258 mmole) of 3,4-dihydrospiro-[(2H)-1-benzopyran-2,3'-piperidine]4-one in 20 mL ethanol was treated with 880 mg (3 mmoles) of 2-(4-methanesulfonamidophenyl)ethyl mesylate and 0.5 g sodium bicarbonate and heated to reflux for 48 hours. The reaction was cooled to room temperature, poured into saturated sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was treated with 1 eq. oxalic acid and the salt was recrystallized from acetone to give product with mp=204°-210° C. Elemental analysis for C22H26N2O4S·C2H2O4 · 1/2H2O Calcd: N, 5.45; C, 56.12; H, 5.69. Found: N, 5.52; C, 56.35; H, 5.54.

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe salt was recrystallized from acetone
  8. customto give product with mp=204°-210° C

Sources & evidence

ORD record
ord-65ca1e4e59264f35b5d4a1e71549ea75
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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