Dicyclohexylcarbodiimide → H-Pro-Gly-OBzl

HRID 2291653Notes

Reaction equation

HRID 2291653 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[NH2:16][CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CC(=O)OCC.CN(C=O)C>[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:16][CH2:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:5]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 409140Benzyl glycinate

Product 1

HCID 10869079H-Pro-Gly-OBzl

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of Boc-Pro-OH, 7.4 g of H-Gly-OBzl, 3.0 ml of NEM and 3.1 g of HOBt are dissolved in 50 ml of EA with the addition of 5 ml of DMF. 4.8 g of DCC are added, and the mixture is left to stir at room temperature for 48 hours. After concentration in vacuo, the residue is dissolved in 50 ml of EA, and the solution is extracted by shaking twice with 30 ml of aqueous citric acid solution and twice with saturated aqueous sodium bicarbonate solution, and the organic phase is dried over sodium sulfate, filtered and evaporated. The residue is dissolved in 10 ml of trifluoroacetic acid, reaction is allowed to take place at room temperature for 1 hour, and the mixture is concentrated in vacuo. The residue crystallizes from EA/pentane.

Workup

  1. waitthe mixture is left
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe residue is dissolved in 50 ml of EA
  4. extractionthe solution is extracted
  5. stirringby shaking twice with 30 ml of aqueous citric acid solution and twice with saturated aqueous sodium bicarbonate solution
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe residue is dissolved in 10 ml of trifluoroacetic acid
  10. customreaction
  11. customat room temperature
  12. customfor 1 hour
  13. concentrationthe mixture is concentrated in vacuo
  14. customThe residue crystallizes from EA/pentane

Sources & evidence

ORD record
ord-0737971fe1944bb49640a99aa8eed1e2
Source dataset
uspto-grants-1989_01
Patent number
US04797471

Reaction notes

Loading…