Dicyclohexylcarbodiimide → 4-methoxybenzyl 4(2-N-benzyloxycarbonyl-L-valyloxyethoxy)benzoate

HRID 489055Notes

Reaction equation

HRID 489055 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:10])=[CH:7][CH:6]=1.[CH2:23]([O:30][C:31]([NH:33][C@H:34]([C:38](O)=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:23]([O:30][C:31]([NH:33][C@H:34]([C:38]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:10])=[CH:21][CH:22]=1)=[O:39])[CH:35]([CH3:37])[CH3:36])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 220358874-Methoxybenzyl 4-(2-hydroxyethoxy)benzoate

Product 1

HCID 233875454-methoxybenzyl 4(2-N-benzyloxycarbonyl-L-valyloxyethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl 4-(2-hydroxyethoxy)benzoate (6.6 g, 21.8 mmole), 4-dimethylaminopyridine (0.61 g, 5 mmole) and N-benzyloxycarbonyl-L-valine (6.3 g, 25 mmole) in dichloromethane (80 ml) was added dicyclohexyl-carbodiimide (5.2 g, 25 mmole) and the mixture was stirred overnight at room temperature. The mixture was cooled and the urethane was filtered. The solution was evaporated and ethyl acetate (200 ml) was added. The organic phase was washed twice with 5% acetic acid, 5% sodium hydrogencarbonate and water. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography with dichloromethane/methanol. Yield: 10.6 g=90%

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe urethane was filtered
  3. customThe solution was evaporated
  4. additionethyl acetate (200 ml) was added
  5. washThe organic phase was washed twice with 5% acetic acid, 5% sodium hydrogencarbonate and water
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe product was isolated by silica gel column chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-ff54fcdfd2fa43cfaab33331239946f6
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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