Water → HCID 53656255, compound

HRID 865485Notes

Reaction equation

HRID 865485 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@H:20]([S:39][CH2:40][C:41]([CH3:48])([CH3:47])[CH2:42][C:43]([O:45]C)=[O:44])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([O:32]C4CCCCO4)([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[OH-].[Na+].O>CO.C1COCC1.CCCCCC.C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@H:20]([S:39][CH2:40][C:41]([CH3:48])([CH3:47])[CH2:42][C:43]([OH:45])=[O:44])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([OH:32])([CH3:30])[CH3:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 54273813HCID 54273813, compound

Product 1

HCID 53656255HCID 53656255, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the product of Step 10 (10.1 g, 0.015 mol) and pyridinium p-toluenesulfonate (1.12 g, 0.045 mol) in a mixture of MeOH:THF 3:1 (80 mL) was warmed to 60° C. overnight. Most of the MeOH was evaporated and an aqueous solution of NH4Cl was added. The product was extracted with EtOAc, washed with brine and dried over Na2SO4. The residual oil was purified by flash chromatography on silica using 1:5 to 1:3 EtOAc:hexane. The product was then dissolved in a mixture of MeOH:THF, 3:1 (70 mL) and the solution was cooled down to 0° C. for the addition of a 1M solution of NaOH in water (35 mL, 0.036 mol). The reaction mixture was stirred 2 days at r.t. Most of the MeOH was evaporated and the solution was acidified with AcOH (acetic acid) to pH ≅5. An aqueous solution of NH4Cl was added and the acid was extracted with EtOAc. The organic phases were washed with brine and dried over Na2SO4. After evaporation of the solvent, the residual oil was purified by flash chromatography using 1:6 to 1:5 EtOAc:hexane (containing 2% AcOH) to give 7.6 g of the title product (87% yield).

Workup

  1. customMost of the MeOH was evaporated
  2. additionan aqueous solution of NH4Cl was added
  3. extractionThe product was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe residual oil was purified by flash chromatography on silica using 1:5 to 1:3 EtOAc
  7. dissolutionThe product was then dissolved in a mixture of MeOH
  8. customMost of the MeOH was evaporated
  9. additionAn aqueous solution of NH4Cl was added
  10. extractionthe acid was extracted with EtOAc
  11. washThe organic phases were washed with brine
  12. dry with materialdried over Na2SO4
  13. customAfter evaporation of the solvent
  14. customthe residual oil was purified by flash chromatography

Sources & evidence

ORD record
ord-27974f88da9242b7ae922e584b80399f
Source dataset
uspto-grants-1996_10
Patent number
US05565473

Reaction notes

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