Water → [4-((2R,3R)-3-([(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-4-oxo-1-phenylazetidin-2-yl)phenoxy]acetic acid

HRID 254068Notes

Reaction equation

[CH3:1][C:2]1([CH3:40])[CH2:7][O:6][C:5]([CH2:14][S:15][C@H:16]2[C:19](=[O:20])[N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:17]2[C:27]2[CH:39]=[CH:38][C:30]([O:31][CH2:32][C:33]([O:35]CC)=[O:34])=[CH:29][CH:28]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1.O.C(N(CC)CC)C>CO>[CH3:1][C:2]1([CH3:40])[CH2:3][O:4][C:5]([CH2:14][S:15][C@H:16]2[C:19](=[O:20])[N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:17]2[C:27]2[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:38][CH:39]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:6][CH2:7]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl [4-((2R,3R)-3-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-4-oxo-1-phenylazetidin-2-yl)phenoxy]acetate (0.86 g, 1.53 mmol) in MeOH (25 ml) was added water (2.5 ml) and triethylamine (1.55 g). The reaction was stirred for 48 h at 50° C. The solvent was evaporated and the residue was purified by preparative HPLC using a gradient of 20-70% CH3CN in 0.1M NH4OAc buffer. Freeze-drying of the pure fractions gave the title compound as a colourless solid. 1H NMR [(CD3)2SO), 400 MHz]□0.50 (s, 3H), 1.15 (s, 3H), 2.93 (d, 1H), 2.96 (d, 1H), 3.21-3.37 (m, 4H), 4.13 (d, 1H), 4.28 (s, 2H), 4.97 (d, 1H), 6.83-7.41 (m, 14H).

Workup

customThe solvent was evaporated
customthe residue was purified by preparative HPLC
customFreeze-drying of the pure fractions

Sources & evidence

ORD record: ord-b8231ca6a6434977ac71612075e8792f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871998B2

Reaction notes

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