Triethylamine → HCID 53990288, compound

HRID 1789895Notes

Reaction equation

HRID 1789895 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH2:19])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH:14]([CH2:17][CH:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][S:3][C:1](=[O:4])[CH3:2])[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 54194372HCID 54194372, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 53990288HCID 53990288, compoundYield 79%

Conditions

Temperature
0 °C

Procedure

Thioacetic acid (5 mL), which had been cooled to 0° C., was added to a mixture of 3-(2-ethoxycarbonyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.72 g; 2.54 mmol) and triethyl amine (0.37 mL; 2.67 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes, at room temperature for 23 hours and then poured onto ice-water (400 mL). The aqueous layer was extracted with CH2Cl2. The combined organic phases were washed with saturated NaHCO3, dried and concentrated under reduced pressure. The crude product was purified by flash chromatography (CH2Cl2/EtOAc: 1/10→68/32) to yield 3-(3-acetylsulfanyl-2-ethoxycarbonyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.72 g, 79%) as an oil.

Workup

  1. additionpoured onto ice-water (400 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washThe combined organic phases were washed with saturated NaHCO3
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (CH2Cl2/EtOAc: 1/10→68/32)

Sources & evidence

ORD record
ord-f22901cbac204dc0a0373c91444823ac
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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