Methanol → HCID 11300622, compound

HRID 1767269Notes

Reaction equation

HRID 1767269 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1)(=[O:4])=[O:3].S(=O)(=O)(O)O.[CH3:24]O>>[CH3:24][O:16][C:15](=[O:17])[CH2:14][CH2:13][C:12](=[O:18])[C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 113692744-(4-(Methylsulfonamido)phenyl)-4-oxobutanoic acid

Product 1

HCID 11300622HCID 11300622, compoundYield 92%

Conditions

Temperature
60 °C

Procedure

4-[(methylsulfonyl)amino]γ-oxobenzenebutanoic acid IIe, (125 g, 0.46 mol) was placed in a flask with 2.5 L of methanol, and 4.6 g of concentrated sulfuric acid (0.047 mol) was added. The slurry was heated to 60° C. for 4 hr, during this period the solids went into solution. After 4 hrs, an aliquot was removed to monitor completion by HPLC. The reaction was determined complete when NMT 2% of the starting material remained. The solution was cooled to 21° C., allowing the product to crystallize. The slurry was cooled to 0° C., and the product was collected by filtration. The filter cake was washed with a mixture of 375 ml of methanol and 12.5 ml of triethylamine (×2), followed by 375 mL of methanol. The title product was obtained in 92% yield (99 area %). Melting point 181-183° C. 1H NMR (400 MHz, DMSO-d6) δ 10.32 (s, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.8 Hz, 2H), 3.58 (s, 3H), 3.2(s, 1H), 3.24 (t, J=6.4 Hz, 2H), 3.1 (s, 3H), 2.63 (t, J=6.4 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ C 196.8, 172.8, 143.0, 131.0; CH 129.6, 117.5; CH2 32.7, 27.6; CH3 51.3, 39.8; MS m/z calcd for C12H14NO5S 284.31 (M−H)+; found 284.00 (M−H)+.

Workup

  1. additionwas added
  2. customan aliquot was removed
  3. temperatureThe solution was cooled to 21° C.
  4. customto crystallize
  5. temperatureThe slurry was cooled to 0° C.
  6. filtrationthe product was collected by filtration
  7. washThe filter cake was washed with a mixture of 375 ml of methanol and 12.5 ml of triethylamine (×2)

Sources & evidence

ORD record
ord-5085c9e82d8e451eb2f987fedc69103a
Source dataset
uspto-grants-2007_06
Patent number
US07232930B2

Reaction notes

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