Ammonium Chloride → (2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester

HRID 411777

반응식

HRID 411777 반응식
[Li]CC[CH2:4][CH3:5].[OH:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=3)[N:16]([CH3:26])[CH:15]=2)=[C:10]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH3:36])[CH:28]=2)[C:9]1=[O:37].[N+](C1C=CC(OC(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=[O:39].[NH2:60][CH:61]([OH:63])C.[NH4+].[Cl-]>C1COCC1>[CH3:36][N:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]([C:10]2[C:9](=[O:37])[N:8]([CH2:7][O:6][C:61](=[O:63])[NH:60][CH2:4][CH2:5][OH:39])[C:12](=[O:13])[C:11]=2[C:14]2[C:22]3[C:17](=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][CH:21]=3)[N:16]([CH3:26])[CH:15]=2)=[CH:28]1

참가 물질

7

반응물 5

HCID 25517Ammonium ChlorideHCID 78756Bis(4-nitrophenyl) carbonateHCID 522583Acetaldehyde ammoniaHCID 98673381-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dioneHCID 178418339Butyllithium

생성물 1

HCID 9892774(2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

n-BuLi (0.96 mL, 1.54 mmol, 1.6 M in hexanes) was added drop-wise to a solution of 1-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (600 mg, 1.54 mmol), prepared as in example la, in THF (30 mL) at 0° C. After 10 min bis(p-nitrophenyl)carbonate (600 mg, 1.96 mmol) was added. The solution was stirred at 0° C. for 20 min. A solution of 1-aminoethanol (128 mg, 2.10 mmol) was added. The resulting mixture was stirred at 0° C. for 30 min. Aqueous NH4Cl was added and the mixture was extracted with EtOAc. The organic extract was washed with brine and dried over MgSO4. Evaporation of the solvents and chromatography of the residue over silica gel using 1:1-3:2 EtOAc/hexanes gave (2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (339 mg, 47%).

후처리

  1. customat 0° C
  2. stirringThe resulting mixture was stirred at 0° C. for 30 min
  3. extractionthe mixture was extracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvents and chromatography of the residue over silica gel using 1:1-3:2 EtOAc/hexanes

출처 및 근거

ORD 기록
ord-ad09b47b9b6040e4ac0dc4c003cf5548
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559164B1

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