L-Glutamic acid, N-[4-(phenylmethoxy)benzoyl]-, dimethyl ester → HCID 15199425, compound

HRID 467239Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1>C(O)C.C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 22 °C

Procedure

To a solution of 5.0 g of N-(4-benzyloxybenzoyl)-L-glutamic acid dimethyl ester in 175 ml ethanol and 25 ml ethyl acetate were added 0.6 g of 5% Pd/C. The mixture was shaken under a hydrogen atmosphere (3 atm) at 22° C. for 3 hours. The reaction mixture was then filtered through Celite and evaporated to an oil which was dissolved in ethyl acetate and, again, filtered through Celite. The filtrate was evaporated to give 3.8 g of the title compound as an oil: 300-MHz 1H NMR (CDCl3) δ2.10-2.21 (m, 1 H), 2.24-2.38 (m, 1 H), 2.41-2.58 (m, 2 H), 3.65 (s, 3 H), 3.79 (s, 3 H), 4.76-4.85 (m, 1 H), 6.86 (d, J=9 Hz, 2 H), 7.11 (d, J=10 Hz, 1 H), 7.67 (d, J=9 Hz, 2 H), 7.78 (b s, 1 H).

Workup

filtrationThe reaction mixture was then filtered through Celite
customevaporated to an oil which
dissolutionwas dissolved in ethyl acetate
filtrationagain, filtered through Celite
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-24aba1a7e78b4180ac92f2eecf41bd3d
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05159079

Reaction notes

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