Triethylamine → 2-Acetylsulfanylmethyl-3-(cis4-tert-butoxycarbonylamino-cyclopent-2-enyl)-propionic acid ethyl ester

HRID 1789902Notes

Reaction equation

HRID 1789902 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].[CH2:5]([O:7][C:8](=[O:25])[C:9]([CH2:11][C@H:12]1[CH2:16][C@@H:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:14]=[CH:13]1)=[CH2:10])[CH3:6].C(N(CC)CC)C>>[CH2:5]([O:7][C:8](=[O:25])[CH:9]([CH2:10][S:3][C:1](=[O:4])[CH3:2])[CH2:11][C@H:12]1[CH2:16][C@@H:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:14]=[CH:13]1)[CH3:6]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 696502532-(cis-4-Tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-acrylic acid ethyl esterHCID 178418634HCID 178418634, compound

Product 1

HCID 867601212-Acetylsulfanylmethyl-3-(cis4-tert-butoxycarbonylamino-cyclopent-2-enyl)-propionic acid ethyl esterYield 65%

Conditions

Temperature
0 °C

Procedure

Thioacetic acid (4 mL), which had been cooled to 0° C., was added to a mixture of 2-(cis4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-acrylic acid ethyl ester (0.56 g, 1.9 mmol) and triethyl amine (0.28 mL, 2.0 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, at room temperature for 19 h and then poured onto ice-water (400 mL). The aqueous layer was extracted with CH2Cl2. The organic phase was washed with saturated NaHCO3, dried and concentrated under reduced pressure to give 1.7 g of the crude product. Purification by flash chromatography (CH2Cl2/EtOAc: 1/0→68/32) afforded 2-acetylsulfanylmethyl-3-(cis4-tert-butoxycarbonylamino-cyclopent-2-enyl)-propionic acid ethyl ester (0.46 g, 65%).

Workup

  1. additionpoured onto ice-water (400 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washThe organic phase was washed with saturated NaHCO3
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto give 1.7 g of the crude product
  7. customPurification by flash chromatography (CH2Cl2/EtOAc: 1/0→68/32)

Sources & evidence

ORD record
ord-f6561cbd5a024ed5996af4867dc9c9cf
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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