Hydrochloric Acid → HCID 58873085, compound

HRID 1990073Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[CH3:9][C:10]1([CH3:26])[C:14]([CH3:16])([CH3:15])[O:13][B:12]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH2:25])=[CH:19][CH:18]=2)[O:11]1.C1CCN2C(=NCCC2)CC1.Cl>ClCCl>[CH3:15][C:14]1([CH3:16])[C:10]([CH3:9])([CH3:26])[O:11][B:12]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH:25][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])=[CH:19][CH:18]=2)[O:13]1

Participants

Conditions

Temperature: 23 °C

Procedure

Add 3-chloropropanesulfonyl chloride (0.285 g, 1.6 mmol) to a suspension of 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethylamine (0.383 g, 1.3 mmol) in dichloromethane (10 mL) at 0° C. Then slowly add DBU (0.457 g, 3.0 mmol) and allow the mixture to warm up to 23° C. Stir 2 h at 23° C. and add more dichloromethane and 1M HCl. Separate layers and wash organic phase with more HCl (×2). Back-extract aqueous phase with dichloromethane (×2). Combine organic phases and wash them with brine, dry over sodium sulfate, concentrate over Celite® and purify by flash chromatography (silica gel), eluting with hexanes-ethyl acetate 3:1 to give 0.333 g of the desired compound as a thick oil. Mass spectrum ESI positive (m/z): 388 (M+1), 410 (M+23).

Workup

washSeparate layers and wash organic phase with more HCl (×2)
washCombine organic phases and wash them with brine
dry with materialdry over sodium sulfate
concentrationconcentrate over Celite®
custompurify by flash chromatography (silica gel)
washeluting with hexanes-ethyl acetate 3:1

Sources & evidence

ORD record: ord-946fb0b2f8fc4b6d89d5a2d6ce737a43
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642361B2

Reaction notes

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