Triethylamine → HCID 67423665, compound

HRID 1393025Notes

Reaction equation

HRID 1393025 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:16][C:15]2[C:6]([CH3:25])([CH:7]3[CH:12]([CH2:13][CH:14]=2)[CH:11]2[CH2:17][CH2:18][CH:19]4[CH:20]([CH3:24])[N:21]([CH3:23])[CH2:22][C:10]24[CH2:9][CH2:8]3)[CH2:5][CH2:4]1.[N+](C1C=CC(O[C:36](=[O:44])[O:37][CH2:38][C:39]2[CH:43]=[CH:42][O:41][CH:40]=2)=CC=1)([O-])=O.C(N(CC)CC)C>C1COCC1>[O:41]1[CH:42]=[CH:43][C:39]([CH2:38][O:37][C:36](=[O:44])[N:2]([CH3:1])[CH:3]2[CH2:16][C:15]3[C:6]([CH3:25])([CH:7]4[CH:12]([CH2:13][CH:14]=3)[CH:11]3[CH2:17][CH2:18][CH:19]5[CH:20]([CH3:24])[N:21]([CH3:23])[CH2:22][C:10]35[CH2:9][CH2:8]4)[CH2:5][CH2:4]2)=[CH:40]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 551434KurchineHCID 18939619HCID 18939619, compound

Product 1

HCID 67423665HCID 67423665, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 7B (10 mg, 0.029 mmol), carbonic acid furan-3-ylmethyl ester 4-nitro-phenyl ester (2.4 mg, 0.032 mmol) and triethylamine (12.0 μL, 0.087 mmol) were dissolved in THF (1 mL) and stirred at room temperature overnight. The crude reaction mixture was purified on silica gel column using 0.5% ammonium hydroxide and 5% methanol in dichloromethane to give the desired product (10.1 mg, 74.2% yield).

Workup

  1. customThe crude reaction mixture
  2. customwas purified on silica gel column

Sources & evidence

ORD record
ord-d644341955cb48a7845f6b9eecf5221f
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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