Water → HCID 178438839, compound

HRID 1422851Notes

Reaction equation

HRID 1422851 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]([SH:15])=[N:13][N:12]=[C:11]3[C:16]3[C:21]([OH:22])=[CH:20][CH:19]=[C:18]([CH:23]([CH3:25])[CH3:24])[C:17]=3O)=[CH:7][CH:8]=2)[CH2:3][C:2]21[O:30]CCO2.O.CC1C=CC(S(O)(=O)=[O:40])=CC=1>CC(C)=O>[OH:22][C:21]1[CH:20]=[C:19]([OH:40])[C:18]([CH:23]([CH3:24])[CH3:25])=[CH:17][C:16]=1[C:11]1[N:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[CH2:1][C:2](=[O:30])[CH2:3]3)[C:14]([SH:15])=[N:13][N:12]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 178439267HCID 178439267, compound

Product 1

HCID 178438839HCID 178438839, compoundYield 902.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 10 (160 mg, 0.38 mmol) was stirred in acetone (7 mL) and water (2 mL) at 63° C. in the presence of p-TsOH (5 mg, cat. amount) for 2 h. After cooled to room temperature, water was added and the reaction mixture was extracted with EtOAc. Combined organic layers were washed with water and brine and dried over Na2SO4. Purification of the concentrated crude product by column chromatography (EtOAc:Hexane=1:1) afforded the title product as a white solid (100 mg, 69%).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washCombined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customPurification of the
  5. concentrationconcentrated crude product by column chromatography (EtOAc:Hexane=1:1)

Sources & evidence

ORD record
ord-e1b53dc80587425ba18d75c4fcfff1e9
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

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