1-Hydroxybenzotriazole → HCID 71547630, compound

HRID 523951Notes

Reaction equation

HRID 523951 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([NH:16][C:17]([N:19]3[CH2:24][CH2:23][C:22]([OH:29])([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]3)=[O:18])[CH:15]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.O[C:52]1[CH:57]=[CH:56][C:55]([C:58]([CH3:70])([CH3:69])[C:59]([O:61]CC2C=CC=CC=2)=[O:60])=[CH:54][CH:53]=1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[F:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([NH:16][C:17]([N:19]3[CH2:20][CH2:21][C:22]([OH:29])([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:24]3)=[O:18])[CH:15]=2)[C:10]([O:12][C:52]2[CH:57]=[CH:56][C:55]([C:58]([CH3:70])([CH3:69])[C:59]([OH:61])=[O:60])=[CH:54][CH:53]=2)=[O:11])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10333334HCID 10333334, compoundHCID 86730100HCID 86730100, compound

Product 1

HCID 71547630HCID 71547630, compoundYield 57.2%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, the compound prepared in Example 37 (75 mg) was dissolved in DMF (1 mL), added with EDC (55.5 mg), HOBt (39.1 mg), diisopropylethylamine (0.05 mL) and benzyl 2-(4-hydroxyphenyl)-2-methylpropanoate (56.5 mg) and stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, sequentially washed with water and a saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent. The resulting residue was dissolved in methanol (1 mL) and ethyl acetate (1 mL), added with 5% palladium carbon (50 mg) and stirred at room temperature for 2 hours in a hydrogen atmosphere. The reaction solution was filtered with celite and the solvent was distilled off. The resulting residue was purified by thin layer chromatography (chloroform:methanol=5:1) to give the titled compound (59.1 mg) having the following physical properties.

Workup

  1. washsequentially washed with water
  2. dry with materiala saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent
  3. dissolutionThe resulting residue was dissolved in methanol (1 mL)
  4. additionethyl acetate (1 mL), added with 5% palladium carbon (50 mg)
  5. stirringstirred at room temperature for 2 hours in a hydrogen atmosphere
  6. filtrationThe reaction solution was filtered with celite
  7. distillationthe solvent was distilled off
  8. customThe resulting residue was purified by thin layer chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-56b65bde852143618d02a27f8ce2b062
Source dataset
uspto-grants-2016_05
Patent number
US09340499B2

Reaction notes

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