Dichloromethane → (2S)-2-(t-butoxycarbonylamino)-3-[4-(1-methyluracil-3-yl)phenyl]propionic acid

HRID 860753Notes

Reaction equation

HRID 860753 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]1[CH:31]=[CH:30][C:28](=[O:29])[NH:27][C:25]1=[O:26].C(N(CC)CC)C.ClCCl>C(O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:27]2[C:28](=[O:29])[CH:30]=[CH:31][N:24]([CH3:23])[C:25]2=[O:26])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 120091-MethyluracilHCID 58746869[(S)-3-(4-boronophenyl)-2-((tertbutoxycarbonyl)amino)propanoic acid]

Product 1

HCID 66839695(2S)-2-(t-butoxycarbonylamino)-3-[4-(1-methyluracil-3-yl)phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 30 mg of (2S)-2-(t-butoxycarbonylamino)-3-[4-(dihydroxyboranyl)phenyl]propionic acid, 25 mg of 1-methyluracil, 27 mg of copper acetate(II), 40 mg of triethylamine and 4 ml of dichloromethane were stirred overnight. The reaction solvent was diluted by ethanol and filtered by Celite filtration. The residual material obtained by concentrating the filtrate was diluted by 1N sodium hydrate and washed with ethyl acetate. After making the water layer acidic by hydrochloric acid, the solution was extracted with ethyl acetate, washed with saturated NaCl aqueous solution, dried with magnesium sulfate and the solvent was removed to obtain a crude material of (2S)-2-(t-butoxycarbonylamino)-3-[4-(1-methyluracil-3-yl)phenyl]propionic acid. This crude material was diluted by 5 ml of ethanol and hexane solution including 2M trimethylsilyldiazomethane was added to give methyl ester. The reaction solvent was concentrated and purified by silica gel chromatography (ethyl acetate-ethanol) to obtain the title compound (7 mg).

Workup

  1. filtrationfiltered by Celite filtration
  2. customThe residual material obtained
  3. concentrationby concentrating the filtrate
  4. additionwas diluted by 1N sodium hydrate
  5. washwashed with ethyl acetate
  6. extractionthe solution was extracted with ethyl acetate
  7. washwashed with saturated NaCl aqueous solution
  8. dry with materialdried with magnesium sulfate
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-7ec04a76c70048ddb85ef94ef5da6e64
Source dataset
uspto-grants-2006_12
Patent number
US07153963B2

Reaction notes

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