Pyridine → HCID 54376120, compound

HRID 382936Notes

Reaction equation

N1C=CC=CC=1.[CH2:7]([O:9][C:10]([C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][OH:19])[O:14][N:13]=1)=[O:11])[CH3:8].[CH:20]1[CH:25]=[CH:24][C:23]([O:26][C:27](Cl)=[S:28])=[CH:22][CH:21]=1>ClCCl>[CH2:7]([O:9][C:10]([C:12]1[CH:16]=[C:15]([CH2:17][CH2:18][O:19][C:27]([O:26][C:23]2[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=2)=[S:28])[O:14][N:13]=1)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

Pyridine (2.4 g, 31 mmol) was added to a stirred solution of 5-hydroxyethylisoxazole-3-carboxylic acid ethyl ester (4.75 g, 26 mmol) (prepared analogously to Example 64 part a) in dichloromethane (150 ml) under nitrogen at room temperature. The mixture was cooled to 0° C. and phenyl chlorothionoformate (5.3 g, 31 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 hand at room temperature for 2 h, then diluted with dichloromethane (200 ml) and washed with water (×2). The organic layer was dried MgSO4) and evaporated in, vacuo. Flash chromatography of the residue on silica gel, eluting with 20% ethyl acetate/hexane, gave the title-compound (6.7 g, 81%), 1H NMR (250 MHz, CDCl3) δ 1.43 (3H, t, J=7.1 Hz, CH3), 3.37 (2H, t, J=6.3 Hz, CH2), 4.46 (2H, q, J=7.1 Hz, CH2), 4.83 (2H, t, J=6.3 Hz, CH2), 6.60 (1H, s, Ar—H), 7.08-7.11 (2H, m, 2 of Ar—H), 7.29 (1H, m, Ar—H), 7.38-7.46 (2H, m, 2 of Ar—H); MS (ES+) m/e 322 [MH]+, m/e 168 [MH—154]+.

Workup

washwashed with water (×2)
customevaporated in, vacuo
washFlash chromatography of the residue on silica gel, eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record: ord-604196e41bf94398b5b61fac37cc48dc
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310203B1

Reaction notes

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