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

HRID 987904ノート

反応式

HRID 987904 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-52650747ef7e4267ab3e1b2ea97c1c85
出典データセット
uspto-grants-2003_10
特許番号
US06632919B1

反応ノート

読み込み中…