Ethanolamine → HCID 178493582, compound

HRID 1947146Notes

Reaction equation

HRID 1947146 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][C@H:30]1[CH2:35][CH2:34][C@H:33]([C:36](O)=[O:37])[CH2:32][CH2:31]1)=[O:28].[NH2:39][CH2:40][CH2:41][OH:42].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(=O)([O-])O.[Na+]>[OH:42][CH2:41][CH2:40][NH:39][C:36]([C@H:33]1[CH2:34][CH2:35][C@H:30]([NH:29][C:27]([C:4]2[N:5]([CH3:26])[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]([CH2:16][C:17](=[O:24])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:8](=[O:25])[C:7]=3[C:3]=2[O:2][CH3:1])=[O:28])[CH2:31][CH2:32]1)=[O:37]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 178493583HCID 178493583, compound

Product 1

HCID 178493582HCID 178493582, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the compound of Example 537 (215 mg, 0.417 mmol), 2-aminoethanol (32.5 μL, 0.542 mmol) and HOBt (84.6 mg, 0.626 mmol) in DMF (5 mL) was added WSCD (120 mg, 0.626 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/methanol=10/0-8/2). Recrystallization of the obtained solid from ethyl acetate-THF gave the title compound (131 mg, 56%) as a white powder.

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/methanol=10/0-8/2)
  7. customRecrystallization of the obtained solid from ethyl acetate-THF

Sources & evidence

ORD record
ord-a52ced8791e84d57b42c775f69512e5a
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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