Diisopropylethylamine → Methyl (2S)-3-(4-biphenylyl)-2-[(2-isopropoxy-3,4-dioxocyclobut-1-enyl)amino]propanoate

HRID 1281909Notes

Reaction equation

HRID 1281909 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5].[CH:21]([O:24][C:25]1[C:26](=O)[C:27](=[O:33])[C:28]=1[O:29]C(C)C)([CH3:23])[CH3:22].CCN(C(C)C)C(C)C>CO>[C:12]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:14][C:9]([CH2:8][C@H:3]([NH:2][C:26]2[C:27](=[O:33])[C:28](=[O:29])[C:25]=2[O:24][CH:21]([CH3:23])[CH3:22])[C:4]([O:6][CH3:7])=[O:5])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1823143,4-Diisopropoxy-3-cyclobutene-1,2-dioneHCID 45357110methyl (2S)-2-amino-3-(4-phenylphenyl)propanoate hydrochloride

Product 1

HCID 86583676Methyl (2S)-3-(4-biphenylyl)-2-[(2-isopropoxy-3,4-dioxocyclobut-1-enyl)amino]propanoateYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl (2S)-2-amino-3-(4-biphenylyl)-propanoate hydrochloride (415 mg, 1142 mmol),3,4-diisopropoxy-3-cyclobutene-1,2-dione (281 mg, 1.42 mmol), DIPEA (247 μl, 1.42 mmol) and MeOH (10 ml) was stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by column chromatography (SiO2; DCM/MeOH, 98:2) to give the title compound (358 mg). δH (DMSO-d6, 390K) 8.50 (1H, d, J 8.0 Hz), 7.63-7.56 (4H, m), 7.47-7.42 (2H, m), 7.36-7.32 (3H, m), 5.24-5.18 (1H, m), 4.80-4.75 (1H, m), 3.74 (3H, s), 3.31 (1H, dd, J 14.2, 5.2 Hz), 3.13 (1H, dd, J, 14.2, 9.4 Hz), 1.38 (3H, d, J 6.0 Hz), 1.37 (3H, d, J 6.1 Hz); m/z (ES+, 70 V) 394 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by column chromatography (SiO2; DCM/MeOH, 98:2)

Sources & evidence

ORD record
ord-1cf98b4fc9a14b00a78dc177bfce27af
Source dataset
uspto-grants-2002_09
Patent number
US06455539B2

Reaction notes

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