Aniline → HCID 86628706, compound

HRID 2422931Notes

Reaction equation

HRID 2422931 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH2:11][C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN(C=O)C.CCN(C(C)C)C(C)C>>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH:10]([CH2:11][C:12](=[O:14])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 131008404-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)butanoic acid

Product 1

HCID 86628706HCID 86628706, compoundYield 56,021.898%

Procedure

To a solution of 33 (0.206 g, 0.657 mmol, 1.2 eq) and aniline (0.051 g, 0.548 mmol) in dry DMF (5 ml) HATU (0.315 g, 0.9087 mmol, 1.5 eq) and DIPEA (0.340 g, 2.63 mmol, 4 eq) was added at room temperature under Ar. After stirring overnight at room temperature, the reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (2×15 ml). The organic extracts were collected, dried over Na2SO4 and the solvent was distilled off under reduced pressure. The crude compound was purified by chromatography on silica gel (3:7 ethyl acetate/hexane, v/v, Rf 0.30) to give 34 as a white solid (0.120 g, 0.307 mol, 47%), mp 165-167° C. 1H NMR (400 MHz, CDCl3) δ 1.43 (9H, s), 2.55 (1H, dd, J 5.0, 13.8 Hz), 2.75 (1H, dd, J 8.4, 13.6 Hz), 3.16-3.39 (2H, m), 3.52-3.57 (1H, m), 4.60 (1H, bs), 7.07-7.13 (3H, m), 7.29-7.32 (4H, m), 7.54 (2H, d, J 8.4 Hz), 8.61 (1H, bs).

Workup

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with ethyl acetate (2×15 ml)
  3. customThe organic extracts were collected
  4. dry with materialdried over Na2SO4
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe crude compound was purified by chromatography on silica gel (3:7 ethyl acetate/hexane, v/v, Rf 0.30)

Sources & evidence

ORD record
ord-6ac6adeef90945bbac55809ee3f82f8d
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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