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

HRID 844229

반응식

HRID 844229 반응식
[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]

참가 물질

4

반응물 2

HCID 5961L-GlutamineHCID 216313-Nitrophthalic anhydride

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
87.5 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a08c992d0ecd423c89c997531ae1e485
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380239B1

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