Hydrochloric Acid → HCID 67419089, compound

HRID 1429354Notes

Reaction equation

HRID 1429354 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([N:21]([CH2:33][C:34]1[CH:43]=[CH:42][CH:41]=[CH:40][C:35]=1[C:36]([O:38]C)=[O:37])[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])(=[O:24])=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+].Cl>O.CO>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH:13]([N:21]([CH2:33][C:34]1[CH:43]=[CH:42][CH:41]=[CH:40][C:35]=1[C:36]([OH:38])=[O:37])[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])(=[O:24])=[O:23])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67418218HCID 67418218, compound

Product 1

HCID 67419089HCID 67419089, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To the solution of compound 2d (100 mg, 0.17 mmol) in H2O (2 mL) and MeOH (10 mL) was added aqueous NaOH (33 mg, 0.84 mmol). The resulting mixture was heated to reflux for 2 hr. Then the mixture was cooled to rt and acidified to pH=3 with 3.5N aqueous HCl, concentrated in vacuo to remove the volatile solvent. The resulting mixture was extracted with EA (2×30 mL). The organic extracts were combined and dried over anhydrous Na2SO4, concentrated in vacuo to give compound 2e as a white solid (80 mg, 80% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hr
  3. concentrationconcentrated in vacuo
  4. customto remove the volatile solvent
  5. extractionThe resulting mixture was extracted with EA (2×30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-144c00bdbecd44298143e5d1ac295410
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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