Triethylamine → HCID 178468199, compound

HRID 1375713Notes

Reaction equation

HRID 1375713 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:20][CH2:21][CH3:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:25]([O:29][C:30](=[O:43])[N:31]=[C:32]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])SC)([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C>CN(C=O)C.[Hg](Cl)Cl>[C:39]([O:38][C:36]([NH:35][C:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:20][CH2:21][CH3:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)=[CH:23][CH:24]=1)=[N:31][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:43])=[O:37])([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 54417798HCID 54417798, compound

Product 1

HCID 178468199HCID 178468199, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

3-{4-[(4-Aminophenethyl)oxy]phenyl}-2(S)-ethoxypropanoic acid (223 mg, 0.61 mmol) and tert-butyl-[(tert-butoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate (186 mg, 0.64 mmol) were mixed in 3 ml DMF. Triethylamine (0.34 ml, 2.44 mmol) was added. The mixture was then cooled in an ice-bath. Mercury (II)chloride (180 mg, 0.66 mmol) was added. After 30 minutes, the cooling bath was removed. The reaction mixture was stirred overnight. Water and ethyl acetate were added into the mixture. The organic phase was separated, dried with magnesium sulfate and the solvent was evaporated in vacuum. Column chromatography of the residue on silica gel using ethyl acetate/heptane (10:90, then 25:75) as eluant gave 135 mg, yield 39% of the desired product.

Workup

  1. temperatureThe mixture was then cooled in an ice-bath
  2. customthe cooling bath was removed
  3. additionWater and ethyl acetate were added into the mixture
  4. customThe organic phase was separated
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-93161d82b73b4a86ba5674734b834c7c
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

Loading…