Sulfuric Acid → HCID 18511992, compound

HRID 1370812Notes

Reaction equation

HRID 1370812 reaction equation
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH:18]1OCC[O:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>O1CCCC1>[CH2:23]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH:18]=[O:19])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18512098HCID 18512098, compound

Product 1

HCID 18511992HCID 18511992, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 40A (1.88 g, 4.83 mmoles) in tetrahydrofuran (30 mL) was treated with an aqueous solution of 2N sulfuric acid (1.24 mL) and allowed to stirr overnight at 65° C. The mixture was cooled to room temperature, quenched with saturated sodium bicarbonate, and concentrated under reduced pressure. The residue was mixed with diethylether and washed with water, brine, dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. MS (ESI+) at m/z 347 (M+H)+.

Workup

  1. customquenched with saturated sodium bicarbonate
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was mixed with diethylether
  4. washwashed with water, brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb88522c709542a299269329c8d2799c
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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