Triethylamine → HCID 178467724, compound

HRID 1375712Notes

Reaction equation

HRID 1375712 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][CH: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][CH: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 229887133-{4-[(4-Aminophenethyl)oxy]phenyl}-2-ethoxypropanoic acid

Product 1

HCID 178467724HCID 178467724, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

3-{4-[(4-Aminophenethyl)oxy]phenyl}-2-ethoxypropanoic acid (20 mg, 0.061 mmol) and tert-butyl-[(tert-butoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate (18.6 mg, 0.064 mmol) were mixed in 0.3 ml DMF. Triethylamine (25.5 ml, 0.183 mmol) was added. The mixture was then cooled in an ice-bath. Mercury (II)chloride (18 mg, 0.066 mmol) was added. After 30 minutes, the cooling bath was removed. The reaction mixture was stirred overnight. Water (1 ml) and ethyl acetate (0.5 ml) were added and then hydromatrix (ca. 0.5 g) was added. After a while, the mixture was filtered. The filtrate was evaporated to dryness. Chromatography of the residue on an ISOLUTE column (SI, 500 mg/3 ml) using ethyl acetate/heptane (10:90, then 25:75, and then 50:50) as eluant gave 15.4 mg, yield 44% of the desired product.

Workup

  1. temperatureThe mixture was then cooled in an ice-bath
  2. customthe cooling bath was removed
  3. additionWater (1 ml) and ethyl acetate (0.5 ml) were added
  4. additionhydromatrix (ca. 0.5 g) was added
  5. filtrationAfter a while, the mixture was filtered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-051d278972bb4c1e8bce68f090d21e80
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

Loading…