Hydrochloric Acid → HCID 59864833, compound

HRID 2423321Notes

Reaction equation

HRID 2423321 reaction equation
[NH2:1][C:2]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][C:14]=2[O:25][CH3:26])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:27])[NH:7]2.N1C(C)=CC=CC=1C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.[OH-].[Na+].Cl>C1COCC1.CCOC(C)=O.O>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43]([NH:1][C:2]2[C:11]([O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=3[O:25][CH3:26])=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6](=[O:27])[NH:7]3)(=[O:45])=[O:44])=[CH:39][CH:38]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 79372,6-LutidineHCID 14798Sodium HydroxideHCID 59864822HCID 59864822, compound

Product 1

HCID 59864833HCID 59864833, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 25.3 (25 mg, 0.068 mmol) and 2,6-lutidine (0.033 mL, 0.28 mmol) in THF (0.1 mL) was added 4-chlorobenzenesulfonyl chloride (30 mg, 0.14 mmol). The mixture was stirred at 70° C. overnight. After cooling, water (0.1 mL) and 10N NaOH (0.1 mL) were added. The mixture was stirred at room temperature for 5 h. 3N HCl (0.35 mL) and EtOAc were added to the mixture, and the organic layer was separated, dried with MgSO4 and concentrated. Flash column chromatography of the residue afforded 25. MS ESI (pos.) m/z: 544.1 (M+H). 1H NMR (DMSO-d6) δ 12.32 (bs, 1H); 11.74 (s, 1H); 10.14 (s, 1H); 8.06 (d, 1H); 7.68 (d, 2H); 7.50 (d, 2H); 7.16 (d, 1H); 6.96 (s, 1H); 6.72 (m, 2H); 6.56 (d, 1H); 6.27 (d, 1H); 3.66 (s, 3H); 3.54 (s, 2H).

Workup

  1. temperatureAfter cooling
  2. stirringThe mixture was stirred at room temperature for 5 h
  3. customthe organic layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-be590255f8e143668854600648b1da68
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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