Triethylamine → HCID 53854503, compound

HRID 1789905Notes

Reaction equation

HRID 1789905 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14]C(C(OCC)=O)=C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:22]1[CH:26]=[CH:25]C=[C:23]1[CH2:27][C:28]([OH:30])=[O:29].C(N([CH2:36][CH3:37])CC)C.C(=O)([O-])[OH:39].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH:27]([C:28]([O:30][CH2:36][CH3:37])=[O:29])[CH2:23][S:22][C:26](=[O:39])[CH3:25])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 159702-Thiopheneacetic acid2×HCID 516892Sodium BicarbonateHCID 53924266HCID 53924266, compound

Product 1

HCID 53854503HCID 53854503, compoundYield 9.4%

Conditions

Temperature
0 °C

Procedure

To crude 4-(2-ethoxycarbonyl-allyl)-piperazine-1-carboxylic acid tert-butyl ester (2.45 g, 8.2 mmol) was added thiolacetic acid (7.5 mL) under argon. The mixture was cooled to 0° C. and triethylamine (1.14 mL, 8.2 mmol) was added dropwise. The mixture was then stirred at room temperature for 2 d and thiolacetic acid (2.5 mL) was added. Stirring was continued for 1 d, then aqueous saturated sodium hydrogencarbonate solution was added carefully until neutral reaction and the mixture was extracted three times with dichloromethane. The combined organic layers were washed twice with aqueous saturated sodium hydrogencarbonate solution and once with brine. After drying over magnesium sulphate the solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, 1.7% methanol in dichloromethane) to give 4-(3-acetylsulfanyl-2-ethoxycarbonyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester (0.29 g, 9.4%).

Workup

  1. stirringStirring
  2. waitwas continued for 1 d
  3. extractionthe mixture was extracted three times with dichloromethane
  4. washThe combined organic layers were washed twice with aqueous saturated sodium hydrogencarbonate solution and once with brine
  5. dry with materialAfter drying over magnesium sulphate the solvent
  6. customwas removed under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, 1.7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-98ac93ea0169462ba5093a6afc91276c
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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