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 411777Notes

Reaction equation

HRID 411777 reaction equation
[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

Participants

7

Reactant 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

Product 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 esterYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-ad09b47b9b6040e4ac0dc4c003cf5548
Source dataset
uspto-grants-2003_05
Patent number
US06559164B1

Reaction notes

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