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p-Toluenesulfonic acid → Boc-Gly-Pro-Glu(O-But)-Gly-OMe

HRID 1461975
Notes
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Reaction equation

HRID 1461975 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([OH:9])=O)=[O:4].[NH2:20][C@H:21]([C:31]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH2:22][CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].S(O)(C1C=CC(C)=CC=1)(=O)=O.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([NH:20][C@H:21]([C:31]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH2:22][CH2:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:9])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 11673468Boc-gly-pro-OHHCID 13419975H-Glu(O-But)-Gly-OMe

Product 1

HCID 131713569Boc-Gly-Pro-Glu(O-But)-Gly-OMe

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

2.7 g (10 mmoles) of Boc-Gly-Pro-OH and 4.5 g (10 mmoles) of H-Glu(O-But)-Gly-OMe.TosOH are dissolved in 20 ml of dimethylformamide. 1.28 ml (10 mmoles) of N-ethylmorpholine and 2.2 g (10.6 mmoles) of dicyclohexylcarbodiimide are added and the mixture is left to stand at room temperature overnight. The dicyclohexylurea is then filtered off, the solvent is distilled off in vacuo, the residue is taken up in ethyl acetate and the solution is washed with citric acid, bicarbonate solution and water, as described above, dried over sodium sulfate and evaporated to dryness. The residue is dissolved in ether and a precipitate is obtained with petroleum ether and filtered off.

Workup

  1. waitthe mixture is left
  2. filtrationThe dicyclohexylurea is then filtered off
  3. distillationthe solvent is distilled off in vacuo
  4. washthe solution is washed with citric acid, bicarbonate solution and water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved in ether
  8. customa precipitate is obtained with petroleum ether
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-26521d3c592341729752d8aab5957ebd
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04457866

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes