Water → N-((7-Methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycine

HRID 987900Notes

Reaction equation

HRID 987900 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:13][C:14]([N:16]([CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17][C:18]([O:20]C)=[O:19])=[O:15])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Li+].[OH-].O>C1COCC1>[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:13][C:14]([N:16]([CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:17][C:18]([OH:20])=[O:19])=[O:15])[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 22987110Methyl N-((7-Methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate

Product 1

HCID 22987124N-((7-Methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycineYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl N-((7-methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-tert-butyloxycarbonylaminoethyl)glycinate (0.775 g, 1.79 mmol) in THF (10 mL, LAB-SCAN C2520, dried over molecular seives) was added LiOH (2M, aqueous) (2.0 mL). The resulting solution was stirred at rt for 30 min, additional water was added, and the THF removed in vacuo. The pH of the aqueous solution was adjusted to pH 3.0 and the precipitate collected, and washed (2×10 mL) by filtration, to yield the desired product (424 mg, 56%) as a colorless precipitate (mp 94-95° C.). 1H NMR (DMSO-d6; this compound exist as two rotamers; chemical shifts for the minor rotamer is given in brackets): δ 12.05 (s br, 1H), 7.90 (7.96) (d, 7.9 Hz, 1H), 7.78 (7.71) (s, 1H), 7.11 (d, 7.9 Hz, 1H), 6.90 (6,73) (m, 1H), 3.97 (4.23) (s, 2H), 3.59 (s, 2H), 3.44 (s, 3H), 3.04 (3.15) (m, 2H), 1.37 (1.36) (s, 9H). 13C NMR (DMSO-d6): δ 170.94 (171.22), 170.00 (170.16), 162.6, 159.1, 155.7, 148.8, 136.30 (136.57), 135.90 (136.09), 128.28 (128.62), 118.12, 111.96 (112.00), 77.9, 48.08 (48.29), 47.5, 38.39 (38.05), 33.44 (33.66), 28.3, 24.2. FAB+ HRMS (m/z): 417.1794, calc. C20H25N4O6 417.1774.

Workup

  1. customthe THF removed in vacuo
  2. customthe precipitate collected
  3. washwashed (2×10 mL)
  4. filtrationby filtration

Sources & evidence

ORD record
ord-cf97879ab9444204a215cffa68f24f28
Source dataset
uspto-grants-2003_10
Patent number
US06632919B1

Reaction notes

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