Triethylamine → HCID 13091025, compound

HRID 1388963Notes

Reaction equation

HRID 1388963 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH3:9][CH:10]([CH2:12][C@@H:13]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:14](ON1C(=O)CCC1=O)=[O:15])[CH3:11].N(CC)(CC)CC>Cl.CN(C=O)C>[NH:24]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C@@H:13]([C:14]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:15])[CH2:12][CH:10]([CH3:11])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 145742L-ProlineHCID 12876461HCID 12876461, compound

Product 1

HCID 13091025HCID 13091025, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Proline (0.842 g, 7.31 mmoles), in its HCl salt form, is dissolved in DMF and stirred with Boc-D-Leu-OSU (2.4 g, 7.31 mmoles) and (C2H5)3N (1.02 ml, 7.31 mmoles), prepared in Step C above, at room temperature overnight. The reaction mixture is filtered and the filtrate is concentrated under vacuum to dryness. The residue is dissolved in ethyl acetate washed with 0.1 N HCl, and then washed twice with H2O. The organic layer is dried over anhydrous Na2SO4 and the solvent removed by evaporation. The crude product is purified by silica gel column, yielding 1.4 g of pure Boc-D-Leu-Pro-OH.

Workup

  1. customprepared in Step C above, at room temperature overnight
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under vacuum to dryness
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with 0.1 N HCl
  6. washwashed twice with H2O
  7. dry with materialThe organic layer is dried over anhydrous Na2SO4
  8. customthe solvent removed by evaporation
  9. customThe crude product is purified by silica gel column

Sources & evidence

ORD record
ord-4d5d95ff419b4b75a7b27854ecaad6e8
Source dataset
uspto-grants-1984_02
Patent number
US04434096

Reaction notes

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