Pyridine → HCID 54718313, compound

HRID 1018387Notes

Reaction equation

[C:1]12([O:11][CH2:12][C:13](O)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][C:29]1([CH3:37])[O:34][C:33](=[O:35])[CH2:32][C:31](=[O:36])[O:30]1.N1C=CC=CC=1>C(Cl)Cl>[C:1]12([O:11][CH2:12][C:13](=[C:32]3[C:33](=[O:35])[O:34][C:29]([CH3:37])([CH3:28])[O:30][C:31]3=[O:36])[OH:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of (adamantan-1-yloxy)-acetic acid (Example 216, step a) (32.3 g, 0.153 mol) and 1,1′-carbonyl-diimidazole (27.6 g, 0.17 mol) in anhydrous DCM (600 ml) was stirred at 0° C. for 15 min, then at room temperature for 75 min. The mixture was concentrated in vacuo (˜300 ml) and the solution was added dropwise over 20 min to a solution of 2,2-dimethyl-1,3-dioxan-4,6-dione (22.1 g, 0.153 mol) and pyridine (30 ml, 0.371 mol) in anhydrous DCM (450 ml) at 0° C. under argon. The mixture was allowed to warm to room temperature and stirred for 16 h. The solution was washed with 2M HCl (2×500 ml), brine (500 ml) and dried (MgSO4). Filtration and evaporation gave the product as a white solid, which was washed with hexane, isolated by filtration and dried (50.1 g, 97%). 1H NMR (300MHz, CDCl3) 4.92 (2H, s), 2.19 (3H, br s), 1.82 (6H, s), 1.74 (6H, s), 1.64 (6H, m).

Workup

waitat room temperature for 75 min
concentrationThe mixture was concentrated in vacuo (˜300 ml)
temperatureto warm to room temperature
stirringstirred for 16 h
washThe solution was washed with 2M HCl (2×500 ml), brine (500 ml)
dry with materialdried (MgSO4)
filtrationFiltration and evaporation

Sources & evidence

ORD record: ord-1cf5751a27324185af5fbaa84391d9a4
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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