Hydrochloric Acid → ethyl 2-(3-aminopropyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate hydrochloride

HRID 579542Notes

Reaction equation

C(N[C:6]([C:8]([N:33]([CH3:37])[C:34](=[O:36])[CH3:35])([CH2:20][CH2:21][CH2:22][CH2:23][B:24]1[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]1)[CH2:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[O:7])(C)(C)C.[ClH:38].[C:39](OCC)(=[O:41])[CH3:40]>>[ClH:38].[NH2:12][CH2:11][CH2:10][CH2:9][C:8]([N:33]([CH3:37])[C:34](=[O:36])[CH3:35])([CH2:20][CH2:21][CH2:22][CH2:23][B:24]1[O:25][C:26]([CH3:31])([CH3:32])[C:27]([CH3:29])([CH3:30])[O:28]1)[C:6]([O:41][CH2:39][CH3:40])=[O:7]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 8857Ethyl Acetate

HCID 66833610tert-butyl 4-(tert-butylcarbamoyl)-4-(N-methylacetamido)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octylcarbamate

Product 1

HCID 66832929ethyl 2-(3-aminopropyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate hydrochloride

Procedure

A solution of tert-butyl 4-(tert-butylcarbamoyl)-4-(N-methylacetamido)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octylcarbamate (140 mg, 0.266 mmol) in ethyl acetate (2 mL) was treated with anh HCl (2 N in ethyl acetate, 10 mL) and stirred at room temp. After 30 min, the solution was concentrated to give crude ethyl 2-(3-aminopropyl)-2-(N-methylacetamido)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate hydrochloride as a white solid (130 mg). ESI MS found for C20H39BN2O5 m/z [399.5 (M+1)]. This material was used without further purification.

Workup

concentrationthe solution was concentrated

Sources & evidence

ORD record: ord-5d55942fe37b46758a107e5228feb61f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040703B2

Reaction notes

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