Ethyl Acetate → Tert-butyl(cis)-3-carbamothioylcyclopentylcarbamate

HRID 2404393Notes

Reaction equation

HRID 2404393 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5]1)(=O)[NH2:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1.C(OCC)(=O)C>O1CCCC1>[C:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5]1)(=[S:26])[NH2:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 59028693cis-3-(Boc-amino)cyclopentanecarboxamide

Product 1

HCID 131731762Tert-butyl(cis)-3-carbamothioylcyclopentylcarbamateYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 120A (0.5 g, 2.2 mmol) in tetrahydrofuran (10 mL) was added Lawesson's reagent (0.53 g, 1.3 mmol). After stirring at room temperature for 5 hours, the reaction mixture was poured into ethyl acetate (50 mL). The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Analogix® Intelliflash280™, SiO2, 0-100% of ethyl acetate in hexanes) to obtain 0.33 g of the title compound. MS (ESI+) M/Z 245 [M+H]+.

Workup

  1. washThe organic layer was washed with saturated NaHCO3 aqueous solution and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (Analogix® Intelliflash280™, SiO2, 0-100% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e7ba1793535d442e9dfe9663a3f9129e
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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