Hydrochloric Acid → HCID 135430884, compound

HRID 323656Notes

Reaction equation

HRID 323656 reaction equation
[Cl:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[C:4]2[C:22]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].[C:30](OC(=O)C)(=[O:32])[CH3:31].C(=O)(O)[O-].[Na+].Cl>N1C=CC=CC=1.O1CCCC1.O.CO>[C:30]([N:19]1[CH2:20][CH2:21][C:22]2[C:4]3[C:5]([S:16][C:17]=2[CH2:18]1)=[N:6][C:7]([CH2:8][N:9]1[C:10](=[O:15])[CH2:11][CH2:12][C:13]1=[O:14])=[C:2]([Cl:1])[C:3]=3[C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)(=[O:32])[CH3:31]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 136386389HCID 136386389, compound

Product 1

HCID 135430884HCID 135430884, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in Example 15 (640 mg) in pyridine (30 ml) was added acetic anhydride (336 mg) while cooling with ice. After stirring for 14 hours at room temperature, the reaction solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (25 ml), washed with water, dried (MgSO4), and then the solvent was distilled off. The residue was subjected to column chromatography on silica gel. The fraction eluted with hexane-ethyl acetate (5:1, v/v) was collected and the solvent was distilled off. The residue thus obtained, which was combined with saturated aqueous sodium bicarbonate (15 ml), methanol (30 ml), water (15 ml) and tetrahydrofurane (30 ml), was stirred for 3 hours at room temperature, and then neutralized with 1N hydrochloric acid. The crystal precipitated was isolated by filtration, and washed with methanol to obtain the title compound (406 mg, 58%). The product was recrystallized from tetrahydrofuran-methanol. A colorless prism crystal. M.p. 300° C. or higher.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (25 ml)
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off
  7. washThe fraction eluted with hexane-ethyl acetate (5:1
  8. customv/v) was collected
  9. distillationthe solvent was distilled off
  10. customThe residue thus obtained
  11. stirringwas stirred for 3 hours at room temperature
  12. customThe crystal precipitated
  13. customwas isolated by filtration
  14. washwashed with methanol

Sources & evidence

ORD record
ord-8f83ece591d74fc2b5deb4b7ee672f8e
Source dataset
uspto-grants-2001_04
Patent number
US06214838B1

Reaction notes

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