Triethylamine → HCID 66621383, compound

HRID 416689Notes

Reaction equation

HRID 416689 reaction equation
NC[CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][OH:8].[C:12]([O:16][C:17]([NH:19][C:20](=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])SC)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([N:33](CC)CC)C.C(OCC)(=O)C>CN(C=O)C.[Hg]Cl>[C:17]([N:19]([CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][OH:8])[C:20]([NH2:33])=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 45091753[3-(2-Aminoethyl)phenyl]methanol

Product 1

HCID 66621383HCID 66621383, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 24182Mercurous ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(aminoethyl)benzyl alcohol (2.3 grams, 0.015 mol, 1 molequivalent), N,N′-bis(tert-butoxycarbonyl)-S-methylisothiourea (4.8 grams, 0.016 mol, 1.1 molequivalent), mercury chloride (4.5 grams, 0.016 mol, 1.1 molequivalent), and triethylamine (7 ml, 0.048 mol, 3 molequivalent) in dry DMF (25 ml) was stirred at room temperature overnight under nitrogen atmosphere. Ethyl acetate (100 ml) was then added and the suspension was filtered over Celite. The filtrate was washed with water, saturated aqueous NH4Cl, and brine, dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography (using a gradient eluent of a 10:90 to 30:70 mixture of EtOAc:hexanes), to give 1.9 grams (32%) of the pure product.

Workup

  1. filtrationthe suspension was filtered over Celite
  2. washThe filtrate was washed with water, saturated aqueous NH4Cl, and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crude product was purified by flash chromatography (
  6. additionto 30:70 mixture of EtOAc

Sources & evidence

ORD record
ord-ffc28dc5951a4143b27ba98045632bfe
Source dataset
uspto-grants-2012_01
Patent number
US08088941B2

Reaction notes

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