Triethylamine → HCID 53934164, compound

HRID 1607105Notes

Reaction equation

HRID 1607105 reaction equation
[C:1]([O:5][C:6](=[O:10])[CH2:7][CH2:8]N)([CH3:4])([CH3:3])[CH3:2].C([N:13](CC)CC)C.[Cl:18][CH2:19][O:20][C:21](Cl)=[O:22]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:10])[CH:7]([NH:13][C:21]([O:20][CH2:19][Cl:18])=[O:22])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62754Chloromethyl chloroformateHCID 4192171tert-Butyl 3-aminopropanoate

Product 1

HCID 53934164HCID 53934164, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

β-alanine t-butylester (316 mg) was dissolved in methylene chloride (2 ml). To this solution were added triethylamine (333 μl: 1.1 molar equivalent) and chloromethylchloroformate (309 mg: 1.1 molar equivalent). The mixture was stirred for 20 minutes while cooling with ice. The reaction solution was concentrated under reduced pressure and was then dissolved in chloroform (20 ml), followed by washing well with water and a saturated solution of sodium chloride. Anhydrous sodium sulfate was applied to dry the chloroform layer which was then concentrated under reduced pressure. The concentrate was purified by silica gel chromatography using a solvent system of chloroform/methanol (200:1 v/v) to obtain the desired substance (394 mg) with a yield of 76%.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionwas then dissolved in chloroform (20 ml)
  4. washby washing well with water
  5. dry with materialto dry the chloroform layer which
  6. concentrationwas then concentrated under reduced pressure
  7. customThe concentrate was purified by silica gel chromatography
  8. customto obtain the desired substance (394 mg) with a yield of 76%

Sources & evidence

ORD record
ord-600ba63b3dc946a59f2107608951d666
Source dataset
uspto-grants-1989_09
Patent number
US04863935

Reaction notes

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