Triethylamine → HCID 54518839, compound

HRID 861892Notes

Reaction equation

[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[O:3].[O:15]=[C:16]([C@@H:34]1[CH2:38][CH2:37][CH2:36][O:35]1)[CH2:17][CH2:18][C@H:19]1[NH:22][C:21](=[O:23])[C@H:20]1[NH:24][C:25](=[O:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C>ClCCCl>[OH:3][CH:2]([N:22]1[C@H:19]([CH2:18][CH2:17][C:16](=[O:15])[C@@H:34]2[CH2:38][CH2:37][CH2:36][O:35]2)[C@H:20]([NH:24][C:25](=[O:33])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]1=[O:23])[C:1]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

p-Methoxybenzyl glyoxylate (3.20 g, 16.5 mmol) in 1,2-dichloroethane (50 ml) was heated at reflux for 1h. using Dean and Stark apparatus. The solution was cooled in ice and treated successively with (3S,4R)-4-[3-oxo-3-[(S)-tetrahydrofuran-2-yl]propyl]-3-phenylacetamidoazetidin-2-one (4.10 g, 12.4 mmol) and triethylamine (170 μl, 1.22 mmol). After stirring at 0° C. for 30 min., the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 50% ethyl acetate in hexane, then ethyl acetate to yield the title compound as a yellow foam (4.53 g, 70%); νmax (CH2Cl2) 3420, 3226, 1769, 1743, 1681, 1613 and 1516 cm-1 ; m/z (FAB, +ve ion, 3-nitrobenzyl alcohol/sodium acetate) 547 (MNa+).

Workup

temperatureat reflux for 1h.
temperatureThe solution was cooled in ice
concentrationthe reaction mixture was concentrated in vacuo
customThe residue was purified by chromatography on silica gel eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-0e2c2959d648429c947232b8eb00f519
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716948

Reaction notes

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