Dicyclohexylcarbodiimide → Benzyl N-(2-benzylacryloyl)glycinate

HRID 2290980Notes

Reaction equation

HRID 2290980 reaction equation
[CH2:1]([C:8](=[CH2:12])[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([O:20][C:21](=[O:24])[CH2:22][NH2:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:13]([O:20][C:21](=[O:24])[CH2:22][NH:23][C:9](=[O:11])[C:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH2:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3035712-Benzylacrylic AcidHCID 409140Benzyl glycinate

Product 1

HCID 13242778Benzyl N-(2-benzylacryloyl)glycinate

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

2.42 g (15 mmoles) of 2-benzyl acrylic acid are dissolved in 30 ml of THF and 10 ml of CHCl3. There is added a solution in 50 ml of THF of 1.87 g of glycine benzyl ester hydrochlorate, 2.2 g of triethylamine, then 2.20 g of HOBT and 3.4 g of DCC. The mixture is stirred for 20 hours at room temperature. The precipitate of DCU formed is collected. After evaporating to dryness and taking up with ethyl acetate the organic phase is washed in succession with 2×20 ml of citric acid, then 3×20 ml of NaHCO3. The material is concentrated under a vacuum and the rest of the DCU formed is suction filtered. A yellow oil which crystallizes slowly is obtained.

Workup

  1. customThe precipitate of DCU formed
  2. customis collected
  3. customAfter evaporating to dryness
  4. washis washed in succession with 2×20 ml of citric acid
  5. concentrationThe material is concentrated under a vacuum
  6. customthe rest of the DCU formed
  7. filtrationfiltered
  8. customA yellow oil which crystallizes slowly
  9. customis obtained

Sources & evidence

ORD record
ord-bd3d94050bf34dc6bcdd581e2b5b1bc1
Source dataset
uspto-grants-1986_10
Patent number
US04618708

Reaction notes

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