Triethylamine → (R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide

HRID 74116Notes

Reaction equation

HRID 74116 reaction equation
[NH2:1][C@H:2]([CH2:13][OH:14])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25]>O1CCCC1>[CH2:6]([NH:5][C:3](=[O:4])[C@H:2]([NH:1][C:22]([O:23][CH2:24][CH3:25])=[O:26])[CH2:13][OH:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10655432(2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

Product 1

HCID 53344986(R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamideYield 73.04%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 250 mL three-neck round bottom flask, 9.65 g (0.0497 mol) (R)-2-amino-N-benzyl-3-hydroxypropionamide, 120 mL tetrahydrofuran, and 7.58 g (0.0749 mol) triethylamine were added in sequence, the mixture was stirred to obtain a solution. At a normal temperature, 6.01 g (0.0554 mol) ethyl chlorocarbonate was added. After the reaction was completed, the solvent was evaporated, and the residue was added with 100 mL water, and stirred uniformly. The solution was extracted with 50 mL×3 ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was evaporated, to obtain a white solid of 9.67 g (0.0363 mol). The molar yield was 73.04%.

Workup

  1. customto obtain a solution
  2. customthe solvent was evaporated
  3. additionthe residue was added with 100 mL water
  4. stirringstirred uniformly
  5. extractionThe solution was extracted with 50 mL×3 ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customto obtain a white solid of 9.67 g (0.0363 mol)

Sources & evidence

ORD record
ord-8967ae5b38804f6ca2b764f681026423
Source dataset
uspto-grants-2014_09
Patent number
US08829226B2

Reaction notes

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