Triethylamine → 2-(([2-(benzylthio)-3,3-dimethoxypropyl]amino}carbonyl)-7-nitro-1H-indol-5-yl pivalate

HRID 1994840Notes

Reaction equation

HRID 1994840 reaction equation
[CH2:1]([S:8][CH:9]([CH:27]([O:30][CH3:31])[O:28][CH3:29])[CH2:10][NH:11][C:12]([C:14]1[NH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([OH:23])=[CH:18][C:17]=2[N+:24]([O-:26])=[O:25])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:39](Cl)(=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41]>O1CCCC1.C(OCC)(=O)C>[C:39]([O:23][C:19]1[CH:20]=[C:21]2[C:16](=[C:17]([N+:24]([O-:26])=[O:25])[CH:18]=1)[NH:15][C:14]([C:12]([NH:11][CH2:10][CH:9]([S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:27]([O:28][CH3:29])[O:30][CH3:31])=[O:13])=[CH:22]2)(=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 59136025N-[2-(benzylthio)-3,3-dimethoxypropyl]-5-hydroxy-7-nitro-1H-indole-2-carboxamide

Product 1

HCID 575032112-(([2-(benzylthio)-3,3-dimethoxypropyl]amino}carbonyl)-7-nitro-1H-indol-5-yl pivalateYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[2-(benzylthio)-3,3-dimethoxypropyl]-5-hydroxy-7-nitro-1H-indole-2-carboxamide (1.0 g) in tetrahydrofuran (10 mL) were added dropwise triethylamine (0.38 mL) and pivaloyl chloride (0.30 mL) under ice-cooling. The mixture was stirred overnight at room temperature, diluted with ethyl acetate, washed with water, 1N hydrochloric acid and saturated brine, dried (MgSO4), and concentrated. The residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (1.18 g, yield 99%) as a pale-yellow amorphous powder.

Workup

  1. temperaturecooling
  2. washwashed with water, 1N hydrochloric acid and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3c1091f023954000a1a6fe7e41183968
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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