Hydrochloric Acid → HCID 71230627, compound

HRID 2199576Notes

Reaction equation

HRID 2199576 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]1[S:14][C:13]([C:15]2[S:16][CH:17]=[CH:18][C:19]=2[CH2:20][C:21]([O:23]C)=[O:22])=[CH:12][CH:11]=1.[OH-].[Na+].Cl>O1CCOCC1>[C:21]([CH2:20][C:19]1[CH:18]=[CH:17][S:16][C:15]=1[C:13]1[S:14][C:10]([C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH2:4][C:3]([OH:25])=[O:2])=[CH:11][CH:12]=1)([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71231148HCID 71231148, compound

Product 1

HCID 71230627HCID 71230627, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Intermediate C (71 mg, 0.181 mmol) was dissolved in dioxane (2 ml) and 1 M NaOH (0.40 ml) and the mixture was stirred at rt overnight. The mixture was acidified by 1 M HCl and aqueous layer extracted with EtOAc. The organic layer was dried (MgSO4) and filtered. Yield: 57 mg (87%); yellow soid. 1H NMR (400 HMz, DMSO-d6): δ 3.73 (s, 4H), 7.09 (d, J 5.2 Hz, 2H), 7.23 (s, 2H), 7.53 (d, J 5.2 Hz, 2H), 12.52 (s, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2e60ad5e5f3b4969904cf8a75d367a87
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

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