Hydrochloric Acid → HCID 86707880, compound

HRID 1481834Notes

Reaction equation

HRID 1481834 reaction equation
[CH3:1][N:2]1[C@:6]2([CH2:18][C:9]3=[N:10][CH:11]=[C:12]([C:14]([O:16]C)=[O:15])[CH:13]=[C:8]3[CH2:7]2)[C:5](=[O:19])[NH:4][C:3]1=[O:20].[OH-].[Li+].Cl>C1COCC1.O>[CH3:1][N:2]1[C@:6]2([CH2:18][C:9]3=[N:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[CH:13]=[C:8]3[CH2:7]2)[C:5](=[O:19])[NH:4][C:3]1=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86707878HCID 86707878, compound

Product 1

HCID 86707880HCID 86707880, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (6R)-3′-methyl-2′,5′-dioxo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,4′-imidazolidine]-3-carboxylate (450 mg, 1.64 mmol) in THF (8 mL) and H2O (2 mL) was added 1 N aqueous lithium hydroxide (1.96 mL, 1.96 mmol). The reaction was stirred at ambient temperature for 2 h, adjusted to pH≈4 by addition of 1 N hydrochloric acid, and concentrated in vacuo to provide the title compound. MS: m/z=262.1 (M+1). 1H NMR (500 MHz, CD3OD) δ 8.96 (s, 1H), 8.24 (s, 1H), 3.54 (d, 1H, J=18.1 Hz), 3.52 (d, 1H, J=17.3 Hz), 3.40 (d, 1H, J=17.3 Hz), 3.39 (d, 1H, J=18.1 Hz), 2.71 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00a967bdc59e44ad8624432d671154c4
Source dataset
uspto-grants-2016_08
Patent number
US09409916B2

Reaction notes

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