Dicyclohexylcarbodiimide → Ac-Gly-Gly-Val-NH2

HRID 128560Notes

Reaction equation

HRID 128560 reaction equation
[NH:1]([C:10]([CH3:12])=[O:11])[CH2:2][C:3]([NH:5][CH2:6][C:7](O)=[O:8])=[O:4].C1CCC(N=C=NC2CCCCC2)CC1.[NH2:28][C@H:29]([C:33]([NH2:35])=[O:34])[CH:30]([CH3:32])[CH3:31]>C(#N)C.O>[NH:1]([C:10]([CH3:12])=[O:11])[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:28][C@H:29]([C:33]([NH2:35])=[O:34])[CH:30]([CH3:32])[CH3:31])=[O:8])=[O:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 97591N-AcetylglycylglycineHCID 445637Valinamide

Product 1

HCID 131719176Ac-Gly-Gly-Val-NH2

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

1.75 g (10 mmoles) Ac-Gly-Gly-OH and 1.73 g (15 mmoles) HONSu were dissolved in 25 ml acetonitrile and cooled to 0° C. 2.46 g DCC (12 mmoles) were then added, the mixture allowed to warm to room temperature and stirred for 2 hours until complete formation of the active ester. After filtering off the DCU, 1.16 g of Val-NH2 free base (10 mmoles) in 25 ml H2O at pH 8 were added slowly and pH maintained above 7. At completion of the reaction the acetonitrile was removed under vacuum and a small residue filtered off from the aqueous phase. The product was then purified by reverse phase HPLC using water/ethanol/acetic acid buffers.

Workup

  1. temperatureto warm to room temperature
  2. additionwere added slowly
  3. temperaturepH maintained above 7
  4. customwas removed under vacuum
  5. filtrationa small residue filtered off from the aqueous phase
  6. customThe product was then purified by reverse phase

Sources & evidence

ORD record
ord-0ea8f293b5984d63aadbfea9c31e01b6
Source dataset
uspto-grants-1995_11
Patent number
US05464821

Reaction notes

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