Lithium hydroxide, monohydrate → HCID 86726880, compound

HRID 924422Notes

Reaction equation

HRID 924422 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:25]([O:27]CC)=[O:26])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([O:22][CH2:23][CH3:24])[N:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>C1COCC1.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:25]([OH:27])=[O:26])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([O:22][CH2:23][CH3:24])[N:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86726879HCID 86726879, compound

Product 1

HCID 86726880HCID 86726880, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution containing ethyl 3-{[(benzyloxy)carbonyl]amino}-7-ethoxy-1,8-naphthyridine-2-carboxylate (47 mg, 0.12 mmol) and lithium hydroxide monohydrate (25 mg, 0.59 mmol) in THF (2.0 mL) and water (1.0 mL) was heated at 65° C. in a sealed vial for 2 h. A precipitate was filtered off and washed with EtOAc to afford the sub-title compound (11 mg). The filtrate was diluted with water (1 mL) and the solution was extracted with EtOAc (2×5 mL). The combined organic extract were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give additional sub-title compound (30 mg). The crude product was used directly in the subsequent reaction. LCMS (ESI) calc. for C19H18N3O5 [M+H]+: m/z=368.1. found: 368.0.

Workup

  1. filtrationA precipitate was filtered off
  2. washwashed with EtOAc

Sources & evidence

ORD record
ord-62496ed97982497b89457625c2019d6d
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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