Hydrochloric Acid → HCID 86707912, compound

HRID 877846Notes

Reaction equation

C(OC([NH:8][C@H:9]1[C:13]2([CH2:16][CH2:15][CH2:14]2)[CH2:12][N:11]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:10]1)=O)(C)(C)C.Cl>>[NH2:8][C@H:9]1[C:13]2([CH2:16][CH2:15][CH2:14]2)[CH2:12][N:11]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:10]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68350426HCID 68350426, compound

Product 1

HCID 86707912HCID 86707912, compound

Procedure

A solution of (S)-benzyl 8-((tert-butoxycarbonyl)amino)-6-azaspiro[3.4]octane-6-carboxylate (0.324 g, 0.900 mmol) in HCl (4.0 N in dioxane) (5.0 mL, 20.00 mmol) was stirred for 1 hr 25 min. +/−MS analysis after 1 hr indicated that essentially no starting material remained (m/e 261.3, M+H for desired product). HCl/dioxane was removed under vacuum, co-evaporated with ether, to yield the hydrochloride salt of the title compound as a white, glassy solid (quantitative yield). +/−MS: m/e 261.3 (M+H), 217.2 (M+M-44 CO2). 1H NMR (400 MHz, METHANOL-d4) d 7.55-7.20 (m, 5H), 5.20-5.07 (m, 2H), 3.67-3.66 (m, 1H), 3.81-3.64 (m, 2H), 3.62-3.47 (m, 2H), 2.26 (d, J=6.2 Hz, 1H), 2.18-1.87 (m, 5H).

Sources & evidence

ORD record: ord-611d6ebb71fb49fc95c5eda91be1e988
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987268B2

Reaction notes

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