Diisopropylethylamine → HCID 86722038, compound

HRID 525020Notes

Reaction equation

HRID 525020 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([O:9][CH3:10])=[O:8].[C:11]([O:15][C:16]([NH:18][C@@H:19]([CH3:23])[C:20](O)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(C(C)C)CC)(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C>[C:11]([O:15][C:16]([NH:18][CH:19]([CH3:23])[C:20]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([O:9][CH3:10])=[O:8])=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 111923Propylphosphonic anhydrideHCID 14104599Methyl 1-amino-1H-pyrrole-2-carboxylate

Product 1

HCID 86722038HCID 86722038, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 1-amino-1H-pyrrole-2-carboxylate (6 g, 48.1 mmol) and (S)-2-(tert-butoxycarbonylamino)propanoic acid (8.10 g, 48.1 mmol) were dissolved in ethyl acetate (40 ml) and cooled in an ice-bath. Under an argon atmosphere, diisopropylethylamine (24.6 ml, 141.2 mmol) was added and, after stirring for 15 min, T3P solution (35.7 ml, 60 mmol, 50% in ethyl acetate) was dropwise added. After stirring for 20 min at 0° C., the reaction was left overnight at room temperature. The reaction mixture was poured onto water and extracted with ethyl ether. The organic phase was washed with water and brine, dried over magnesium sulphate and the solvent evaporated under reduced pressure. 8.6 g (83% yield) of the final product was obtained and use in the next synthetic step without further purification.

Workup

  1. temperaturecooled in an ice-bath
  2. stirringAfter stirring for 20 min at 0° C.
  3. waitthe reaction was left overnight at room temperature
  4. additionThe reaction mixture was poured onto water
  5. extractionextracted with ethyl ether
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-f0037c3630c9461e926e479d2d11306e
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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