Sodium Hydroxide → HCID 69482109, compound

HRID 2364533Notes

Reaction equation

[OH:1][C@@H:2]([CH2:28][OH:29])[CH2:3][NH:4][C:5]([C:7]1[C:8](=[O:27])[N:9]([CH3:26])[C:10]2[C:15]([C:16]=1[OH:17])=[N:14][CH:13]=[C:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH:11]=2)=[O:6].[OH-].[Na+:31]>>[OH:1][C@@H:2]([CH2:28][OH:29])[CH2:3][NH:4][C:5]([C:7]1[C:8](=[O:27])[N:9]([CH3:26])[C:10]2[C:15]([C:16]=1[O-:17])=[N:14][CH:13]=[C:12]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[CH:11]=2)=[O:6].[Na+:31]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 69482110HCID 69482110, compound

Product 1

HCID 69482109HCID 69482109, compoundYield 94%

Procedure

In a manner similar to that described in example 474, from N-[(2R)-2,3-dihydroxypropyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (395 mg, 0.985 mmol described in example 516) and 1 N sodium hydroxide (0.99 mL) was prepared sodium 3-({[(2R)-2,3-dihydroxypropyl]amino}carbonyl)-7-[(4-fluorophenyl)methyl]-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olate (390 mg, 94% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.61 (s, 1 H), 8.17 (s, 1 H), 7.60 (s, 1 H), 7.33-7.29 (m, 2 H), 7.11-7.06 (m, 2 H), 4.85 (m, 1 H), 4.57 (m, 1 H), 4.02 (s, 2 H), 3.50 (m, 1 H), 3.38 (s, 3 H), 3.40-3.25 (m, 3 H), 3.16 (m, 1 H); MS m/z 402 (M+1).

Sources & evidence

ORD record: ord-2b695473456d40f68bcd142e3eec49a1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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