Butyl glycinate → [5-(4-Chloro-phenoxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid butyl ester

HRID 250322Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:16]([OH:18])=O)[C:10](=[CH:14][CH:15]=2)[C:11]([OH:13])=O)=[CH:4][CH:3]=1.[CH2:21]([O:25][C:26](=[O:29])[CH2:27][NH2:28])[CH2:22][CH2:23][CH3:24]>>[CH2:21]([O:25][C:26](=[O:29])[CH2:27][N:28]1[C:16](=[O:18])[C:9]2[C:10](=[CH:14][CH:15]=[C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][CH:19]=3)[CH:8]=2)[C:11]1=[O:13])[CH2:22][CH2:23][CH3:24]

Participants

Reactant 2

HCID 76155Butyl glycinate

HCID 667130414-(4-Chloro-phenoxy)-phthalic acid

Product 1

HCID 66713943[5-(4-Chloro-phenoxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid butyl esterYield 65.8%

Conditions

Temperature: 250 °C

Procedure

A mixture of 500 mg 4-(4-Chloro-phenoxy)-phthalic acid and glycine n-butyl ester (286 mg) was heated at 250° C. for 5 min. The reaction mixture was purified by chromatography with dichloromethane as eluent to give 436 mg the title compound. 1H NMR (200 MHz, DMSO) δ 7.48 (d, J=8.6 Hz, 1H), 7.59 (d, J=9.0 Hz, 2H), 7.46 (m, 2H), 7.29 (d, J=9.0 Hz, 2H), 4.46 (s, 2H), 4.16 (t, J=6.2 Hz, 2H), 1.61 (m, 2H), 1.38 (m, 2H), 0.92 (t, J=7.0 Hz, 3H).

Workup

customThe reaction mixture was purified by chromatography with dichloromethane as eluent

Sources & evidence

ORD record: ord-3189b29a306a4d35be1c402f0f923470
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863292B2

Reaction notes

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