Diisopropylethylamine → HCID 178500466, compound

HRID 19301Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[CH:4]([NH2:11])[CH2:5][C@H:6]1[CH2:9][C@H:8]([CH3:10])[CH2:7]1.C(N(CC)C(C)C)(C)C.[Cl:22][C:23]1[CH:56]=[CH:55][CH:54]=[CH:53][C:24]=1[O:25][C:26]1[CH2:30]N([C@@H](CC2CCCCC2)C(NC2C=CN(CC(O)(C)C)N=2)=O)[C:28](=[O:52])[CH:27]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[CH:4]([N:11]1[CH2:30][C:26]([O:25][C:24]2[CH:53]=[CH:54][CH:55]=[CH:56][C:23]=2[Cl:22])=[CH:27][C:28]1=[O:52])[CH2:5][C@H:6]1[CH2:7][C@H:8]([CH3:10])[CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a small pressure bottle was placed a mixture of 2-amino-3-(trans-3-methyl-cyclobutyl)-propionic acid methyl ester (147 mg, 0.86 mmol), acetonitrile (6 mL) and N,N-diisopropylethylamine (220 μL, 1.03 mmol) which was heated to 80° C. To this mixture was added (E)-4-bromo-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester (prepared as in Example 61, 276 mg, 0.86 mmol) and the tube sealed and heated at 100° C. overnight. The mixture was cooled to room temperature and concentrated in vacuo with silica gel (2 g). Purification by Biotage flash chromatography (40S column, 16% ethyl acetate/hexanes to 40% ethyl acetate/hexanes) afforded 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(trans-3-methyl-cyclobutyl)-propionic acid methyl ester (108 mg, 35%) as an amber oil: HR-ES-MS m/z calculated for C19H22NO4Cl [M+H]+ 364.1310, observed 364.1310.

Workup

customthe tube sealed
temperatureheated at 100° C. overnight
temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo with silica gel (2 g)
customPurification by Biotage flash chromatography (40S column, 16% ethyl acetate/hexanes to 40% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-f0fc045e911f4bed8df125a60ba4f7b9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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