L-Glutamine → 2-(4-Nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid

HRID 844229

反応式

HRID 844229 の反応式
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][C@H:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19](=[O:21])[NH2:20]>CN(C=O)C>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:5]=1[C:10](=[O:11])[N:15]([CH:16]([CH2:17][CH2:18][C:19](=[O:21])[NH2:20])[C:22]([OH:24])=[O:23])[C:7]2=[O:9])([O-:3])=[O:2]

参加物

4

反応物 2

HCID 5961L-GlutamineHCID 216313-Nitrophthalic anhydride

生成物 1

HCID 155498382-(4-Nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
87.5 °C

実験手順

A mixture of 3-nitrophthalic anhydride (1.5 g, 7.8 mmol) and L-glutamine (1.14 g, 7.8 mmol) in DMF (15 mL) is heated at 85-90° C. for 4 hours. The mixture is concentrated in vacuo and the residue is slurried with water (30 mL). The resulting slurry is filtered and the solid is washed with water (10 mL), dried (60° C., <1 mm Hg) to give 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid (1.82 g, 73%); mp 182-184° C.; 1H NMR (DMSO-d6) δ8.33 (d, J=7.7 Hz, 1H), 8.22 (d, J=7.0 Hz, 1H), 8.11 (t, J=7.8 Hz, 1H), 7.19 (s, 1H), 6.73 (s, 1H), 4.82-4.77 (dd, J=4.6 and 9.8 Hz, 1H), 2.36-2.11 (m, 4H); 13C NMR (DMSO-d6) δ173.21, 170.03, 165.43, 162.75, 144.45, 136.70, 132.98, 128.83, 127.25, 122.52, 51.87, 31.31, 23.87; Anal. Calcd. For C13H11N3O7: C, 48.60; H, 3.45; N, 13.08. Found: C, 48.52; H, 3.28; N, 13.05.

後処理

  1. concentrationThe mixture is concentrated in vacuo
  2. filtrationThe resulting slurry is filtered
  3. washthe solid is washed with water (10 mL)
  4. customdried (60° C., <1 mm Hg)

出典と根拠

ORDレコード
ord-a08c992d0ecd423c89c997531ae1e485
出典データセット
uspto-grants-2002_04
特許番号
US06380239B1

関連ノート

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