Diisopropylethylamine → HCID 66899348, compound

HRID 19384Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].[CH2:12]([O:14][C:15](=[O:31])/[CH:16]=[C:17](/[O:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[N:24][N:25]2[CH3:30])\[CH2:18]Br)[CH3:13].C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([NH:6][CH2:18]/[C:17](/[O:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[N:24][N:25]2[CH3:30])=[CH:16]\[C:15]([O:14][CH2:12][CH3:13])=[O:31])[CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (L)-leucine methyl ester hydrochloride (0.043 g, 0.24 mmol), (E)-4-bromo-3-(1-methyl-1H-indazol-4-yloxy)-but-2-enoic acid ethyl ester (0.073 g, 0.22 mmol) and N,N-diisopropylethylamine (0.070 g, 0.54 mmol) in acetonitrile (6 mL) in a sealed tube was heated at 90° C. for 18 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0% to 100% diethyl ether/hexanes) to afford (S)-2-[(E)-3-ethoxycarbonyl-2-(1-methyl-1H-indazol-4-yloxy)-allylamino]-4-methyl-pentanoic acid methyl ester (0.055 g, 66%).

Workup

temperatureThe reaction mixture was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (silica gel, 0% to 100% diethyl ether/hexanes)

Sources & evidence

ORD record: ord-8b290bcf390042e0b95370b415f4435e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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