Dicyclohexylcarbodiimide → HCID 15614978, compound

HRID 620225Notes

Reaction equation

HRID 620225 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1(N=C=NC2CCCCC2)CCCCC1.[C:32]([NH:42][C@H:43]([C:45](O)=[O:46])[CH3:44])([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>C(Cl)Cl>[C:32]([NH:42][C@H:43]([C:45]([N:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3]2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:46])[CH3:44])([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 736104N-carbobenzyloxyalanineHCID 15614976Ethyl N-(2,3-dihydro-1H-inden-5-yl)glycinate

Product 1

HCID 15614978HCID 15614978, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl N-(5-indanyl)-glycinate (10.6 g, 48.4 mmol) and N,N'-dicyclohexylcarbodiimide (10.5 g, 50.8 mmol) in 200 ml CH2Cl2 at 0° C. was added dropwise a solution of N-carbobenzyloxy-L-alanine (11.3 g, 50.8 mmol) in 100 ml CH2Cl2. After the addition was completed the solution was stirred 10 min., warmed to room temperature and stirred overnight. The solution was filtered and concentrated in vacuo. The residue was dissolved in ether, filtered, washed with saturated NaHCO3, 10% aqueous HCl (5x), brine and dried MgSO4). Concentration of the volatiles in vacuo provided the product.

Workup

  1. additionAfter the addition
  2. stirringstirred overnight
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ether
  6. filtrationfiltered
  7. washwashed with saturated NaHCO3, 10% aqueous HCl (5x), brine and dried MgSO4)
  8. customConcentration of the volatiles in vacuo provided the product

Sources & evidence

ORD record
ord-77c0d499d4224b3299ab81c279511935
Source dataset
uspto-grants-1989_04
Patent number
US04820729

Reaction notes

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