Hydrochloric Acid → HCID 69056522, compound

HRID 227638Notes

Reaction equation

HRID 227638 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([O:26]C)=[O:25])=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[Na+].Cl>CO.C1COCC1.O.[Cl-].[Na+].O>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=4)[C:24]([OH:26])=[O:25])=[O:19])=[CH:13][CH:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69061426HCID 69061426, compound

Product 1

HCID 69056522HCID 69056522, compoundYield 86.4%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of Example 348A (0.5 g, 1.19 mmol) in methanol (50 mL) and THF (20 mL) was treated with 2N NaOH (3.6 mL, 7.2 mmol), stirred at room temperature for 4 hours, and heated to reflux for 1 hour. The mixture was cooled to room temperature, diluted with water, acidified to pH 3 with 4N HCl, and diluted with brine resulting in the formation of a precipitate. The solid was collected by filtration and dried to give 0.417 g of the desired product. MS (ESI(+)) m/e 406 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 7.41 (m, 3H); 7.55 (s, 1H); 7.56 (d, J=6.0 Hz, 1H); 7.66-7.71 (m, 3H); 8.14 (s, 1H); 8.47 (s, 1H); 9.30 (s, 1H); 9.32 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationThe solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-979eb4e40f654b5294ff026b9cfb67c9
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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