L-Threonine → 3-Hydroxy-2-(4-phenylethynyl-benzoylamino)-butyric acid methyl ester

HRID 422965Notes

Reaction equation

HRID 422965 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4].[CH3:9]CN(C(C)C)C(C)C.[C:18]1([C:24]#[C:25][C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.CCOC(C)=O>[CH3:9][O:7][C:6](=[O:8])[CH:2]([NH:1][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:27][CH:28]=1)[CH:3]([OH:4])[CH3:5]

Participants

6

Reactant 3

HCID 6288L-ThreonineHCID 81531Diisopropylethylamine2×HCID 43089034-(2-Phenylethynyl)benzoic acid

Product 1

HCID 666772683-Hydroxy-2-(4-phenylethynyl-benzoylamino)-butyric acid methyl esterYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of threonine (1.66 g, 9.8 mmol) and DIEA (1.53 ml, 8.8 mmol) in DMF (10 ml) was added to a stirred solution of 4-phenylethynyl-benzoic acid 3 (1.55 g, 7.0 mmol) and DIEA (1.53 ml, 8.8 mmol) in DMF (11 ml) at rt. After 12 h, the reaction was diluted with EtOAc (300 ml) and washed with 0.5M HCl (2×60 ml), sat. aq. NaHCO3 (60 ml), 50% diluted brine (60 ml), sat. brine (60 ml), dried with Na2SO4, filtered and concentrated under reduced pressure. Upon drying in vacuo, 2.34 g of white solid was obtained (approximately quantitative yield in 99% purity).

Workup

  1. washwashed with 0.5M HCl (2×60 ml), sat. aq. NaHCO3 (60 ml), 50% diluted brine (60 ml), sat. brine (60 ml)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customUpon drying in vacuo

Sources & evidence

ORD record
ord-0543cc425b2343e9b8736a9425e4746d
Source dataset
uspto-grants-2012_01
Patent number
US08101640B2

Reaction notes

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