4-Methylmorpholine → Boc-Pro-Gly-NH2

HRID 743145Notes

Reaction equation

HRID 743145 reaction equation
[NH2:1][CH2:2][C:3]([NH2:5])=[O:4].Cl.C[O-].[Na+].[N:10]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CO.CN(C=O)C>[N:10]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([NH:1][CH2:2][C:3]([NH2:5])=[O:4])=[O:14]

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2723639Glycinamide hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 7256544Boc-Pro-Gly-NH2

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

0.56 mg (5 mmol) of H-Gly-NH2.HCl are dissolved in 20 ml MeOH and 270 mg (5 mmol) NaOMe added. Stirring takes place for 10 min and the solvent is removed under vacuum. To the residue are added 15 ml DMF, 1.07 g (5 mmol) Boc-Pro-OH, 1.2 g (6.0 mmol) EDCI, 0.9 g (6 mmol) HOBT and 0.825 ml (7.5 mmol) NMM and stirring takes place for 16 hours. To the reaction mixture are added 10 g of mixed-bed ion exchanger (Merck ion exchanger V), stirring takes place for 0.5 hours, followed by filtering and washing with 10 ml MeOH. The filtrate is concentrated under vacuum, the resulting oil absorbed in 150 ml ethyl acetate and the organic phase washed three times with 10 ml 0.5N HCl, 10% NaHCO3 solution and H2O respectively.

Workup

  1. customfor 10 min
  2. customthe solvent is removed under vacuum
  3. stirringstirring
  4. customfor 16 hours
  5. stirringstirring
  6. customfor 0.5 hours
  7. filtrationby filtering
  8. washwashing with 10 ml MeOH
  9. concentrationThe filtrate is concentrated under vacuum
  10. customthe resulting oil absorbed in 150 ml ethyl acetate
  11. washthe organic phase washed three times with 10 ml 0.5N HCl, 10% NaHCO3 solution and H2O respectively

Sources & evidence

ORD record
ord-c1fdc066edbf4779a8cb11ae4b5999b7
Source dataset
uspto-grants-1996_09
Patent number
US05556836

Reaction notes

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