Triethylamine → HCID 66939591, compound

HRID 1257354Notes

Reaction equation

HRID 1257354 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:35])[O:32][CH2:33][CH3:34]>O1CCCC1>[CH2:33]([O:32][C:31]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][CH:3]=1)=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 58127606HCID 58127606, compound

Product 1

HCID 66939591HCID 66939591, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an ice-bath, to a solution (4 mL) of the crude compound (0.84 mmol) obtained in Example 36b in tetrahydrofuran were added triethylamine (0.15 ml, 1.1 mmol) and ethyl chlorocarbonate (79 ml, 1.0 mmol), and the mixture was stirred at room temperature overnight. After confirmation of the termination of the reaction by TLC, the resulting salt was removed. The solvent was evaporated under reduced pressure. The resulting crude title compound was recrystallized (hexane-ethyl acetate) to give the title compound (180 mg, 54% in 2 steps) as colorless crystals.

Workup

  1. customAfter confirmation of the termination of the reaction by TLC
  2. customthe resulting salt was removed
  3. customThe solvent was evaporated under reduced pressure
  4. customThe resulting crude title compound was recrystallized (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-fbb1d578734448a1be5fa3b6f37b3daa
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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