Water → HCID 25132944, compound

HRID 916560Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2(OCCN3CCC4(N(CC5C=CC=CC=5)C(=O)NC4)CC3)[CH2:13]C[N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:43][CH2:44][CH:45]1[O:49][CH2:48][CH2:47][O:46]1.[OH2:50].[CH3:51][C:52](C)([O-:54])C.[K+]>CN(C=O)C.[Cl-].[Na+].O>[C:10]([C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)([CH2:43][CH2:44][CH:45]1[O:49][CH2:48][CH2:47][O:46]1)[C:13]([O:54][CH2:52][CH3:51])=[O:50])#[N:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1 (7.02 g, 27.32 mmol) and 2-(2-bromoethyl)-1,3-dioxolane compound 2 (3.85 mL, 32.78 mmol) in anhydrous DMF (100 mL), potassium t-butoxide (32.78 mL, 1 M in t-BuOH) was added. The content was heated to 80° C. and stirred overnight. H2O (400 mL) and brine (200 mL) were added to the content and the mixture was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. Flash column chromatography with hexane/ethyl acetate (6/1) afforded 9.5 g brown oil (˜85% product+˜15% SM). 1H NMR (400 MHz, CDCl3) δ[ppm]: 7.66 (1H, d, J=2.3 Hz), 7.48 (1H, d, J=8.4 Hz), 7.40 (1H, dd, J=8.4 Hz, 2.2 Hz), 4.91 (1H, t, J=4.4 Hz), 4.30-4.20 (2H, m), 3.98-3.94 (2H, m), 3.86-3.83 (2H, m), 2.48 (1H, td, J=12.2 Hz, 4.5 Hz), 2.24 (1H, td, J=12.2 Hz, 4.3 Hz), 1.88-1.81 (1H, m), 1.75-1.68 (1H, m), 1.24 (3H, t, J=7.1 Hz). 13C NMR (400 MHz, CDCl3) δ[ppm]: 166.90, 134.68, 133.70, 131.28, 128.60, 125.88, 117.58, 103.04, 65.26, 63.91, 53.22, 32.24, 29.88, 14.06.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-bc7e195bef254839b54a9faad26e56ca
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271172B2

Reaction notes

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