Triethylamine → HCID 20285488, compound

HRID 127620Notes

Reaction equation

HRID 127620 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:24]([S:27][CH2:28][CH:29]([CH3:33])[C:30](Cl)=[O:31])(=[O:26])[CH3:25]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[CH2:7][N:8]([C:30](=[O:31])[CH:29]([CH3:33])[CH2:28][S:27][C:24](=[O:26])[CH3:25])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 20285438N-Cycloheptylglycine 1,1-dimethylethyl ester

Product 1

HCID 20285488HCID 20285488, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and chilled (0°-5° C.) solution of N-cycloheptylglycine t-butyl ester (32.9 g, 0.12 mol) and triethyl amine (13.2 g, 0.13 mol) in methylene chloride (150 ml) was added dropwise 3-acetylthio-2-methylpropanoyl chloride (21.6 g, 0.12 mol) dissolved in 50 ml methylene chloride. The reaction mixture was stirred overnight. Filtration of the reaction mixture followed by washing the filtrate with saturated sodium bicarbonate (500 ml), brine (500 ml), 5% HCL (4×500 ml), brine (500 ml), saturated aqueous sodium bicarbonate (3×500 ml), brine (500 ml); drying the organic layer over Na2SO4 and MgSO4 ; filtration; and solvent evaporation afforded a nearly quantitative yield of the desired compound (44 g, crude).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationFiltration of the reaction mixture
  3. washby washing the filtrate with saturated sodium bicarbonate (500 ml), brine (500 ml), 5% HCL (4×500 ml), brine (500 ml), saturated aqueous sodium bicarbonate (3×500 ml), brine (500 ml)
  4. dry with materialdrying the organic layer over Na2SO4 and MgSO4
  5. filtrationfiltration
  6. customand solvent evaporation

Sources & evidence

ORD record
ord-640364a04e4345e8bc3a096ecf87f2b8
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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