Water → 2-(2-Morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid monoethyl ester

HRID 1830143Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[C:5]([CH2:20][C:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([O:8]CC)=[O:7])[CH3:2].O>C(O)C>[CH2:1]([O:3][C:4](=[O:29])[C:5]([CH2:20][C:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-(2-morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid diethyl ester (934 mg, 2.3 mmol) in a 2:1 mixture of ethanol and water (12 ml) LiOH.H2O (193.3 mg, 4.61 mmol) was added and heated at 40° C. for 19 hrs. Ethanol was evaporated under reduced pressure, the residual aqueous mixture was acidified to pH 1 and extracted with methylene chloride (2×40 ml). The organic extract was dried with MgSO4 and evaporated under reduced pressure to give 2-(2-morpholin-4-yl-2-oxo-ethyl)-2-(3-phenyl-propyl)-malonic acid monoethyl ester as a thick, yellow oil (831 mg); 1H NMR (CDCl3) 7.4–7.1 (m, 6H), 4.25 (q, J=7.1 Hz, 2H), 3.8–3.4 (m, 8H), 3.20 (d, J=16.4 Hz, 1H), 2.9 (d, J=16.4 Hz, 1H), 2.6 (m, 2H), 2.1–1.8 (m, 4H), 1.25 (t, J=7.1 Hz, 3H). MS: 378 (MH+).

Workup

additionwas added
customEthanol was evaporated under reduced pressure
extractionextracted with methylene chloride (2×40 ml)
extractionThe organic extract
dry with materialwas dried with MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-a4b5faf3309946cbac4cc243669ceb71
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064123B1

Reaction notes

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