Triethylamine → HCID 13599173, compound

HRID 543260Notes

Reaction equation

HRID 543260 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:22]([S:25][CH2:26][CH:27]([CH3:31])[C:28](Cl)=[O:29])(=[O:24])[CH3:23]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[CH2:7][N:8]([C:28](=[O:29])[CH:27]([CH3:31])[CH2:26][S:25][C:22](=[O:24])[CH3:23])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 13298943Tert-butyl 2-(cyclopentylamino)acetate

Product 1

HCID 13599173HCID 13599173, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 60 g (0.30 mol) of N-cyclopentylglycine t- butyl ester and 75 ml (0.54 mol) of triethylamine in 200 ml of methylene chloride at 0° C. was added dropwise a solution of 54 g (0.30 mol) of 3-acetylthio-2-methylpropanoyl chloride in 250 ml of methylene chloride. After the reaction mixture was stirred at room temperature overnight, it was filtered and concentrated in vacuo. The residue was taken up in ethyl acetate and wasned once with saturated aqueous NaHCO3, once with brine, three times with 5% aqueous HCl, once with brine, and five times with saturated aqueous NaHCO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to yield 80.1 g (78%) of N-(3-acetylthio-2-methylpropanoyl)-N-cyclopentylglycine t-butyl ester as an oil which crystallized on standing.

Workup

  1. filtrationit was filtered
  2. concentrationconcentrated in vacuo
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1630b6d28f804b31b97916da0921ee40
Source dataset
uspto-grants-1987_04
Patent number
US04661515

Reaction notes

Loading…