Triethylamine → HCID 86629356, compound

HRID 1175143Notes

Reaction equation

HRID 1175143 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6](Cl)=[O:7])[CH3:2].C[O:11][C:12](=O)[CH2:13][C:14]1([NH2:17])[CH2:16][CH2:15]1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([NH:17][C:14]1([CH2:13][CH:12]=[O:11])[CH2:16][CH2:15]1)=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 516892Sodium BicarbonateHCID 45078843Methyl (1-aminocyclopropyl)acetate

Product 1

HCID 86629356HCID 86629356, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chlorocarbonyl-acetic acid ethyl ester (2.75 ml; 22.1 mmol) is added dropwise under stirring and cooling to a solution of (1-amino-cyclopropyl)-acetic acid methyl ester (Chemstep Product List, 13926) (3.00 g; 23.2 mmol) in triethylamine (6.4 ml; 46.2 mmol) and CH2Cl2 (150 ml). After stirring at room temperature for 30 minutes, the reaction mixture is poured on a saturated solution of NaHCO3 and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness. Purification via chromatography (SiO2; hexane/acetone 6:4) yield the title compound as crystalline light-yellow solid (1.9 g; 34%) 1H-NMR (400 MHz; DMSO-d6): 8.40 (s, 1H); 4.07 (q, 2H); 3.60 (s, 3H); 3.12 (s, 2H); 2.58 (s, 2H); 1.17 (t, 3H); 0.71 (m, 2H); 0.66 (m, 2H). MS (m/z) ES+: 244 (MH+)

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. extractionextracted with CH2Cl2 three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification via chromatography (SiO2; hexane/acetone 6:4)

Sources & evidence

ORD record
ord-70cf1596e7df4a9a8703d269cb378c29
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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