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

HRID 741875Notes

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, 1H), 2.24-2.38 (m, 1H), 2.41-2.58 (m, 2H), 3.65 (s, 3H), 3.79 (s, 3H), 4.76-4.85 (m, 1H), 6.86 (d, J=9 Hz, 2H), 7.11 (d, J=10 Hz, 1H), 7.67 (d, J=9 Hz, 2H), 7.78 (bs, 1H).

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-dd338afc2bb744e182d07e8289b6e707
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05552545

Reaction notes

Loading…