Dicyclohexylcarbodiimide → HCID 23387547, compound

HRID 489042Notes

Reaction equation

HRID 489042 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[CH2:20]([O:27][C:28]([NH:30][C@H:31]([C:35](O)=[O:36])[CH:32]([CH3:34])[CH3:33])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:20]([O:27][C:28]([NH:30][C@H:31]([C:35]([O:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1)=[O:36])[CH:32]([CH3:34])[CH3:33])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 22035731HCID 22035731, compound

Product 1

HCID 23387547HCID 23387547, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 4-methoxybenzyl 4-hydroxycyclohexanoate (7.5 g, 28 mmole), 4-dimethylaminopyridine (0.73 g, 6 mmole) and N-benzyloxycarbonyl-L-valine (7.54 g, 30 mmole) in dichloromethane (90 ml) was added dicylohexyl-carbodiimide (6.8 g, 33 mmole) and the mixture was stirred for 2 days at room temperature. The mixture was cooled and the urethane was filtered. The solution was evaporated and 250 ml ethyl acetate 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 toluene/acetone. Yield: 13 g=93%

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe urethane was filtered
  3. customThe solution was evaporated
  4. addition250 ml ethyl acetate 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 toluene/acetone

Sources & evidence

ORD record
ord-8daa78a32a9340a4a4274b905bd0579d
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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