Hydrochloric Acid → HCID 46866263, compound

HRID 1970803Notes

Reaction equation

HRID 1970803 reaction equation
[CH2:1]([C:8]1[C:9]([N:20](S(CC2C=CC=CC=2)(=O)=O)[S:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:23])=[O:22])=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([C:8]1[C:9]([NH:20][S:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:23])=[O:22])=[N:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 46866262HCID 46866262, compound

Product 1

HCID 46866263HCID 46866263, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Benzyl-2-bis(benzylsulfonyl)amino-5-phenylpyrazine (c-42) (1.15 g, 2.02 mmol) was suspended in methanol (24 mL), and to this was added 10% (w/v) aqueous solution of sodium hydroxide (5.7 mL) while stirring at room temperature and then stirred at 65° C. for 30 min. After cooling to room temperature, to this was added 2 M hydrochloric acid to stop the reaction and extracted twice with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated under reduced pressure with a rotary evaporator. The residue was recrystallized from ethyl acetate to give 3-benzyl-2-benzylsulfonylamino-5-phenylpyrazine (dideoxycoelenterasulfonamide) (c-37) as a colorless solid (662 mg, 78.9%). Rf=0.62 (n-hexane/ethyl acetate=3/2). Mp. 207-208.5° C. UV (MeOH, 0.3% DMSO) λmax (log ε) 322.5 (4.01), 285.5 (4.08), 261 (4.14). UV (pH 7.4 PB, 0.3% DMSO) λmax (log ε) 343 (4.01), 280.5 (4.07). 1H NMR (400 MHz, DMSO-d6) δ 4.26 (s, 2H), 4.94 (s, 2H), 7.15-7.21 (m, 1H), 7.23-7.30 (m, 4H), 7.36 (s, 5H), 7.40-7.53 (m, 3H), 8.04 (d, J=7.0 Hz, 2H), 8.95 (s, 1H), 10.55 (s, 1H). 13C NMR (75.5 MHz, DMSO-d6/CD3OD=2/1) δ 38.5, 60.1, 126.7 (2C), 126.8, 128.8 (2C), 128.9, 129.0 (2C), 129.4 (2C), 129.5 (2C), 129.7, 130.4, 131.4 (2C), 136.3, 137.3, 138.5, 145.8, 146.3, 146.6. IR (KBr, cm−1) 447, 515, 532, 546, 615, 664, 692, 748, 783, 889, 1117, 1157, 1179, 1323, 1400, 1425, 1450, 1495, 3034, 3267. HRMS (FAB+) m/z 416.1429 (M+H, C24H22N3O2S requires 416.1433).

Workup

  1. stirringstirred at 65° C. for 30 min
  2. temperatureAfter cooling to room temperature
  3. customthe reaction
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removing anhydrous sodium sulfate
  8. filtrationby filtration
  9. concentrationthe filtrate was concentrated under reduced pressure with a rotary evaporator
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-aabd5006c085415aa6a044d395c6e5d7
Source dataset
uspto-grants-2013_04
Patent number
US08431525B2

Reaction notes

Loading…