Ethanolamine → HCID 59625421, compound

HRID 2192862Notes

Reaction equation

HRID 2192862 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([C:35]([OH:37])=O)[N:11]([C:16]([C:18]1[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[N:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[N:22][CH:23]=1)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:38][CH2:39][CH2:40][OH:41].C(N(C(C)C)CC)(C)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(=O)([O-])O.[Na+]>[C:24]([C:21]1[N:20]=[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)[C:18]([C:16]([N:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[C@H:10]([C:35]([NH:38][CH2:39][CH2:40][OH:41])=[O:37])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:17])=[CH:23][N:22]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59625450HCID 59625450, compound

Product 1

HCID 59625421HCID 59625421, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-[(tert-Butoxycarbonyl)amino]-N-({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)-N-(2-methylpropyl)-L-alanine (125 mg), 2-aminoethanol (60 mg) and diisopropylethylamine (250 μl) were dissolved in DMF (10 ml), BOP reagent (500 mg) was added and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:1-1:0) was concentrated under reduced pressure to give the object compound (110 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. washthe fraction eluted with ethyl acetate-hexane (0:1-1:0)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-107fd3270b1c4328bf70433f18869c93
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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