1,1'-Carbonyldiimidazole → 1-(1,4-Dioxo-4-phenylbutyl)-L-proline methyl ester

HRID 903431Notes

Reaction equation

HRID 903431 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:27][O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1>O1CCCC1>[CH3:27][O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:11](=[O:13])[CH2:10][CH2:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 728713-Benzoylpropionic acidHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 139329111-(1,4-Dioxo-4-phenylbutyl)-L-proline methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.56 g. of 3-benzoylpropionic acid and 3.24 g. of N,N-carbonyldiimidazole in 30 ml. of tetrahydrofuran is stirred at room temperature for 30 minutes. A 3.32 g. portion of L-proline methyl ester hydrochloride is added and the mixture is stirred at room temperature for 2.5 days. The solvent is removed in vacuo. Water and dichloromethane are added to the residue and the organic layer is separated, washed with water, then with 0.1 N hydrochloric acid and dried over magnesium sulfate. The solvent is removed in vacuo, giving 5.0 g. of the desired product as off-white crystals, m.p. 66°-70° C.

Workup

  1. additionA mixture of 3.56 g
  2. customThe solvent is removed in vacuo
  3. additionWater and dichloromethane are added to the residue
  4. customthe organic layer is separated
  5. washwashed with water
  6. dry with materialwith 0.1 N hydrochloric acid and dried over magnesium sulfate
  7. customThe solvent is removed in vacuo
  8. customgiving 5.0 g

Sources & evidence

ORD record
ord-c6f98c2042a24ee48528f9fc20a98441
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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