Water → N-((5-Methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycine

HRID 987904Notes

Reaction equation

HRID 987904 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([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:6](=[O:12])[NH:7]2.[Li+].[OH-].O>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([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:6](=[O:12])[NH:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 22987119Methyl N-((5-Methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate

Product 1

HCID 22987121N-((5-Methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycineYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl N-((5-methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate (0.72 g, 1.70 mmol) in THF (10 mL) was added LiOH (aqueous, 2M) (2.0 mL). The resulting solution was stirred at rt. for 45 min. then additional water was added, the THF was evaporated in vacuo and the pH of the aqueous solution was adjusted to 3.0. The resulting precipitate was washed with water (2×10 mL), collected by centrifugation and dried in vacuo to yield the desired product (366 mg, 53%) as a white powder (mp 133-36° C.). 1H NMR (DMSO-d6; this compound exist as two rotamers; chemical shifts for the minor rotamer is given in brackets): δ 12.12 (s br, 1H), 8.33 (d, J=4.9 Hz, 1H), 8.00 (s, 1H), 7.09 (d, J=4.9 Hz, 1H), 6.92 (6.70) (m, 1H), 3.99 (4.26) (s, 2H), 3.62 (s, 2H), 3.45 (m, 2H+H2O), 3.17 (m, 2H), 2.53 (2.52) (s, 3H), 1.36 (1.34) (s, 9H) 13C NMR (DMSO-d6): δ 171.07 (171.31), 170.23 (170.54), 162.36, 155.80, 149.53, 149.27, 145.30, 132.67 (133.55), 129.35 (129.20), 119.92, 113.44, 78.01, 48.13, 47.33, 38.60 (38.36), 34.07, 28.27, 17.76. FAB− HRMS (m/z): 417.1798, calc. C20H26N4O6−H 417.1774.

Workup

  1. customthe THF was evaporated in vacuo
  2. washThe resulting precipitate was washed with water (2×10 mL)
  3. customcollected by centrifugation
  4. customdried in vacuo

Sources & evidence

ORD record
ord-52650747ef7e4267ab3e1b2ea97c1c85
Source dataset
uspto-grants-2003_10
Patent number
US06632919B1

Reaction notes

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