Triethylamine → HCID 59605845, compound

HRID 1945542Notes

Reaction equation

HRID 1945542 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH2:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][Cl:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Product 1

HCID 59605845HCID 59605845, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-aminoazetidine-1-carboxylic acid tert-butyl ester (730 mg, 4.24 mmol) and triethylamine (1.74 mL, 1.29 g, 12.72 mmol) in DCM (10 mL) was cooled to 0° C. before the addition of 4-chlorobutyrylchloride (523 μL, 657 mg, 4.66 mmol). The resulting mixture was stirred for 16 h then quenched with H2O and extracted with DCM. The combined organic extracts were washed with brine then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 30-70%) affording 3-(4-Chlorobutyrylamino)azetidine-1-carboxylic acid tert-butyl ester as a brown oil (1.04 g, 89%).

Workup

  1. customthen quenched with H2O
  2. extractionextracted with DCM
  3. washThe combined organic extracts were washed with brine
  4. dry with materialthen dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 30-70%)

Sources & evidence

ORD record
ord-0e0d771f2a9a484d87c61093922d8ba3
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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