Cysteamine → 4-Hydroxy-3-[7-(2-methoxy-4-methylsulfanyl-phenyl)-2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl]-6-methyl-pyran-2-one

HRID 982867Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][C:14]=1[O:21][CH3:22].[NH2:24][CH2:25][CH2:26][SH:27]>C(O)C>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10]1[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])[S:27][CH2:26][CH2:25][N:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-Hydroxy-3-[(E)-3-(2-methoxy-4-methylsulfanyl-phenyl)-acryloyl]-6-methyl-pyran-2-one (41.8 mg, 0.126 mmol), prepared as in Reference 5, Step 5.1, was dissolved in absolute ethanol (5 mL) and then 2-aminoethanethiol (9.8 mg, 0.126 mmol) was added to the solution. The mixture was stirred at 80° C. The progress of the reaction was followed by analytical HPLC and when complete (approximately 12 hours) the solvent was removed in vacuo. Product was purified by silica flash column chromatography to provide 4-hydroxy-3-[7-(2-methoxy-4-methylsulfanyl-phenyl)-2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl]-6-methyl-pyran-2-one (20.5 mg) as a pale, yellow solid. LCMS: MH+ 392.6.

Workup

customwas followed by analytical HPLC and when complete (approximately 12 hours)
customwas removed in vacuo
customProduct was purified by silica flash column chromatography

Sources & evidence

ORD record: ord-d51a8ea00f0d4dfb80a9107b8abdcaed
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06861419B2

Reaction notes

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