Dicyclohexylcarbodiimide → HCID 54215249, compound

HRID 1413127Notes

Reaction equation

HRID 1413127 reaction equation
[C:1]([O:5][C:6](=[O:23])[C@H:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1)([CH3:4])([CH3:3])[CH3:2].[C:24]([S:28][CH2:29][CH:30]([CH3:34])[C:31](O)=[O:32])(=[O:27])[CH2:25][CH3:26].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([O:5][C:6](=[O:23])[C@H:7]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:31](=[O:32])[CH:30]([CH3:34])[CH2:29][S:28][C:24](=[O:27])[CH2:25][CH3:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11723418HCID 11723418, compoundHCID 12764104HCID 12764104, compound

Product 1

HCID 54215249HCID 54215249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-Prolyl-L-phenylalanine tert-butyl ester (0.54 g) was added to a solution of 3-propanoylthio-2-methylpropanoic acid (0.30 g) and dicyclohexylcarbodiimide (0.35 g) in dichloromethane (10 ml) cooled in an ice bath. The mixture was stirred in the ice bath for one hour and then at room temperature overnight, followed by concentration under reduced pressure. Ethyl acetate was added to the residue. After cooling, the precipitates were filtered off. The filtrate was washed, dried and concentrated as in Example 26. The residue was chromatographed as in Example 26 to give 1-(3-propanoylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationat room temperature overnight, followed by concentration under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. temperatureAfter cooling
  5. filtrationthe precipitates were filtered off
  6. washThe filtrate was washed
  7. customdried
  8. concentrationconcentrated as in Example 26
  9. customThe residue was chromatographed as in Example 26

Sources & evidence

ORD record
ord-9cfb754b6ee1430ba90b1027ad31a613
Source dataset
uspto-grants-1981_02
Patent number
US04248883

Reaction notes

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