1-Hydroxybenzotriazole → HCID 57860106, compound

HRID 1947144Notes

Reaction equation

HRID 1947144 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].[CH3:36][S:37]([CH2:40][C:41](O)=[O:42])(=[O:39])=[O:38].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(=O)([O-])O.[Na+]>[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:31][CH2:32][N:33]([C:41](=[O:42])[CH2:40][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:34][CH2:35]1)=[O:28]

Participants

6

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 37328412-Methanesulfonylacetic acidHCID 57860479HCID 57860479, compound

Product 1

HCID 57860106HCID 57860106, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the compound of Example 77 (200 mg, 0.423 mmol), (methylsulfonyl)acetic acid (76.0 mg, 0.550 mmol) and HOBt (85.8 mg, 0.635 mmol) in DMF (4 mL) was added WSCD (122 mg, 0.635 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extract was combined, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate). Recrystallization of the obtained solid from ethyl acetate gave the title compound (60.3 mg, 24%) as white crystals.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate)
  7. customRecrystallization of the obtained solid from ethyl acetate

Sources & evidence

ORD record
ord-ac20bbafacca43ed92ed8dc972af178f
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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