Hydrogen Bromide → Methyl 2-amino-2-(furan-2-yl)acetate hydrobromide

HRID 530197Notes

Reaction equation

HRID 530197 reaction equation
[BrH:1].C(OC([NH:12][CH:13]([C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)[C:14]([O:16][CH3:17])=[O:15])=O)C1C=CC=CC=1.CCOCC>C(O)(=O)C>[BrH:1].[NH2:12][CH:13]([C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 14085234Methyl 2-(((benzyloxy)carbonyl)amino)-2-(furan-2-YL)acetate

Product 1

HCID 118647338Methyl 2-amino-2-(furan-2-yl)acetate hydrobromideYield 99.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To magnetically stirred 33 wt % hydrogen bromide (2.00 ml, 11.04 mmol) in acetic acid was added methyl 2-(((benzyloxy)carbonyl)amino)-2-(furan-2-yl)acetate (579 mg, 2 mmol). After stirring at room temperature for 1 hr, 25 mL of anhydrous ether was added to give methyl 2-amino-2-(furan-2-yl)acetate hydrobromide (468 mg, 1.983 mmol, 99% yield) as a grey solid. 1H NMR (400 MHz, DMSO-d6) δ 8.93 (s, 2H), 7.81 (dd, J=1.8, 0.8 Hz, 1H), 6.69 (m, 1H), 6.57 (dd, J=3.3, 1.9 Hz, 1H), 5.61 (s, 1H), 3.78 (s, 3H).

Sources & evidence

ORD record
ord-dd52a65ef8ba42229851d9563121ab8a
Source dataset
uspto-grants-2016_05
Patent number
US09353060B2

Reaction notes

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