Hydrochloric Acid → 2-Cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethanesulfonic acid thiazol-2-ylamide

HRID 1159470Notes

Reaction equation

C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][S:24]([NH:27][C:28]2[S:29][CH:30]=[CH:31][N:32]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[CH:33]1([CH2:38]I)[CH2:37][CH2:36][CH2:35][CH2:34]1.Cl>C1COCC1.CN1C(=O)N(C)CCC1.CCOC(C)=O>[S:29]1[CH:30]=[CH:31][N:32]=[C:28]1[NH:27][S:24]([CH:23]([C:20]1[CH:19]=[CH:18][C:17]([S:14]([CH3:13])(=[O:16])=[O:15])=[CH:22][CH:21]=1)[CH2:38][CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)(=[O:25])=[O:26]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of diisopropylamine (1.0 mmol, 0.10 g) in 7 mL of THF and 3 mL of DMPU at 0° C. is added n-BuLi (0.61 mL, 2.5 M in hexane) and the reaction mixture is stirred for 15 min, then cooled to −78° C. The title C compound, C-(4-methane-sulfonyl-phenyl)-N-thiazol-2-yl-methanesulfonamide (0.693 mmol, 0.23 g) is added and the reaction mixture is allowed to warm to 0° C. After 1 h, the reaction is recooled to −78° C., cyclopentylmethyliodide (0.72 mmol, 0.15 g) is added and the reaction is allowed to warm to RT over 3 h. The reaction mixture is poured into aqueous 1 N HCl, and the product is taken up in EtOAc, dried and evaporated to afford an orange oil. Chromatography on silica affords 2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethanesulfonic acid thiazol-2-ylamide: 1H NMR δ 11.6 (br s, 1H), 7.84 (d, J=8, 2H), 7.58 (d, J=8, 2H), 6.67 (d, J=4.5, 1H), 6.39 (d, J=4.5, 1H); 4.27 (m, 1H), 3.03 (s, 3H), 2.04-2.2 (m, 1H), 1.12-1.61 (m, 10H); e/z (ES) 415 (M+1, 100%).

Workup

temperatureto warm to 0° C
waitAfter 1 h
customis recooled to −78° C.
temperatureto warm to RT over 3 h
customdried
customevaporated
customto afford an orange oil

Sources & evidence

ORD record: ord-ac13b4f8b68d44e899333ebce96fe51b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812167B2

Reaction notes

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