Hydrochloric Acid → HCID 135934895, compound

HRID 1970807Notes

Reaction equation

HRID 1970807 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:14]([NH:17][S:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)(=[O:20])=[O:19])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].Cl>CO>[CH2:29]([C:13]1[C:14]([NH:17][S:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)(=[O:20])=[O:19])=[N:15][CH:16]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)[N:12]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67003450HCID 67003450, compound

Product 1

HCID 135934895HCID 135934895, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Acetoxyphenyl)-3-benzyl-2-[(4-hydroxybenzyl)sulfonylamino]pyrazine (c-48) (105 mg, 214 μmol) was dissolved in methanol (2 mL) and to this was added 10% (w/v) aqueous solution of sodium hydroxide (1.0 mL) while stirring at room temperature and then stirred at 60° C. for 2 h. After cooling to room temperature, to this was added 2 M hydrochloric acid to stop the reaction, and extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After removing a anhydrous sodium sulfate by filtration, the filtrate was concentrated under reduced pressure with a rotary evaporator. The residue was purified by column chromatography (10 g, n-hexane/ethyl acetate=1/1). Recrystallization from n-hexane/ethyl acetate gave 3-benzyl-2-(4-hydroxybenzyl)sulfonylamino-5-(4-hydroxyphenyl)pyrazine (coelenterasulfonamide) (c-38) as a yellow solid (43.4 mg, 45.2%). Rf=0.29 (n-hexane/ethyl acetate=1/1). Mp. 194.5-196.5° C. 1H NMR (400 MHz, DMSO-d6) δ 4.22 (s, 2H), 4.78 (s, 2H), 6.70-6.77 (AA′BB′, 2H), 6.83-6.90 (AA′BB′, 2H), 7.10-7.21 (m, 3H), 7.23-7.31 (m, 4H), 7.85-7.95 (AA′BB′, 2H), 8.81 (s, 1H), 9.54 (s, 1H), 9.81 (s, 1H), 10.30 (s, 1H). 13C NMR. (67.8 MHz, DMSO-d6) δ 38.0, 59.1, 115.4 (2C), 115.8 (2C), 119.9, 126.3, 126.6, 127.7 (2C), 128.3 (2C), 129.0 (2C), 132.0 (2C), 135.9, 138.2, 144.4, 145.7, 146.4, 157.7, 158.8. IR (KBr, cm−1) 536, 602, 700, 835, 889, 1119, 1155, 1177, 1258, 1275, 1327, 1402, 1456, 1514, 1611, 3529, 3412, 3487. Anal. Calcd. For C24H21N3O4S: C, 64.41; H, 4.73; N, 9.39. Found: C, 64.28; H, 4.74; N, 9.28.

Workup

  1. stirringstirred at 60° C. for 2 h
  2. temperatureAfter cooling to room temperature
  3. customthe reaction
  4. extractionextracted 3 times with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removing a anhydrous sodium sulfate
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated under reduced pressure with a rotary evaporator
  10. customThe residue was purified by column chromatography (10 g, n-hexane/ethyl acetate=1/1)
  11. customRecrystallization from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-2462520623e44d22a9047933c18baa05
Source dataset
uspto-grants-2013_04
Patent number
US08431525B2

Reaction notes

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