Isobutylamine → HCID 86616773, compound

HRID 1725618Notes

Reaction equation

HRID 1725618 reaction equation
[O:1]=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][CH:4]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[C:5]([OH:7])=O.[CH2:21]([NH2:25])[CH:22]([CH3:24])[CH3:23].Cl.CN(C)CCCN=C=NCC.O.N1(O)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(Cl)Cl>[CH2:21]([NH:25][C:5](=[O:7])[CH:4]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][C:2](=[O:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:22]([CH3:24])[CH3:23]

Participants

9

Reactant 6

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5696304-Oxo-4-phenyl-2-[(trifluoroacetyl)amino]butanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 86616773HCID 86616773, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-oxo-4-phenyl-2-[(trifluoroacetyl)amino]butanoic acid (3.9 g, 13.5 mmol), isobutylamine (2.68 mL, 27.0 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (5.17 g, 27.0 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (3.64 g, 27.0 mmol), and N,N-diisopropylethylamine (11.7 mL, 67.4 mmol) was stirred overnight at room temperature in dimethylformamide (20 mL). The reaction was worked up with methylene chloride and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Chromatography (silica gel, 0 to 20% ethyl acetate in hexane gradient elution), gave the title compound as a yellow solid (1.41 g). MS 345 (M+1). 1H NMR (500 MHz, CDCl3) □ 7.95 (d, J=7.3 Hz, 2H), 7.92 (bs, 1H), 7.63 (t, J=7.4 Hz, 1H), 7.50 (t, J=7.7 Hz, 2H), 6.86 (bs, 1H), 5.02-4.99 (m, 1H), 3.78 (dd, J=18.3, 2.4 Hz, 1H), 3.33 (dd, J=18.3, 9.0 Hz, 1H), 3.10 (t, J=6.4 Hz, 2H), 1.81-1.73 (m, 1H), 0.88 (d, 6H).

Workup

  1. washThe organic extracts were washed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washChromatography (silica gel, 0 to 20% ethyl acetate in hexane gradient elution)

Sources & evidence

ORD record
ord-ae9b258d82244df8ac21beaf6f5e3d9f
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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