Aniline → HCID 11842829, compound

HRID 1422878Notes

Reaction equation

HRID 1422878 reaction equation
CCN=C=NCCCN(C)C.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C@H:25]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:26](O)=[O:27]>C1COCC1.CCOC(C)=O>[C:33]([O:32][C:30](=[O:31])[NH:29][C@H:25]([C:26](=[O:27])[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][Br:19])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11255774HCID 11255774, compound

Product 1

HCID 11842829HCID 11842829, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDCI (2.10 g, 11.1 mmol) and aniline (0.68 ml, 7.5 mmol) were added to a solution of 7.4 mmol of (S)-7-bromo-2-tert-butoxycarbonylamino-heptanoic acid (Gupta P. K., et al., Bioorg. Med. Chem. Lett., 2010, 20, 23, 7067) in THF (70 ml) and the reaction mixture was stirred overnight at RT. The solvent was removed under reduced pressure and the crude reaction mixture was diluted with AcOEt, washed with water and then with 10% aqueous citric acid and finally with saturated NaHCO3. After removal of the solvent under reduced pressure and purification on silica gel (n-hexane/AcOEt: 1/9) the desired adduct was obtained.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude reaction mixture
  3. washwashed with water
  4. customAfter removal of the solvent
  5. customunder reduced pressure and purification on silica gel (n-hexane/AcOEt: 1/9) the desired adduct
  6. customwas obtained

Sources & evidence

ORD record
ord-2a61829aa0594910afc608793da662d2
Source dataset
uspto-grants-2015_01
Patent number
US08927533B2

Reaction notes

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