Dicyclohexylcarbodiimide → HCID 11784295, compound

HRID 620229Notes

Reaction equation

HRID 620229 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([NH:25][C@H:26]([C:28](O)=[O:29])[CH3:27])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:15]([NH:25][C@H:26]([C:28]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:29])[CH3:27])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80908N-Benzylglycine ethyl esterHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 11784295HCID 11784295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl N-benzyl-glycinate (47.5 g, 0.268 mol) and N-carbobenzyloxy-L-alanine (60.0 g, 0.268 mol) in 600 ml of methylene chloride at 0° C. was added dropwise a solution of N,N'-dicyclohexylcarbodiimide (55.2 g, 0.268 mol) in 600 ml methylene chloride over a 1 hour period. After the addition was complete the solution was stirred for 10 min., warmed to room temperature and continued stirring overnight. The solution was filtered, washed with dilute aqueous HCl, H2O, saturated NaHCO3, brine, dried (MgSO4). Concentration of the solution in vacuo yielded the oily product.

Workup

  1. additionAfter the addition
  2. stirringcontinued stirring overnight
  3. filtrationThe solution was filtered
  4. washwashed with dilute aqueous HCl, H2O, saturated NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. customConcentration of the solution in vacuo yielded the oily product

Sources & evidence

ORD record
ord-4ee6dc96caee42aca4186cea78b623df
Source dataset
uspto-grants-1989_04
Patent number
US04820729

Reaction notes

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