Triethylamine → HCID 59558469, compound

HRID 1175138Notes

Reaction equation

HRID 1175138 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]1([NH2:9])[CH2:8][O:7][CH2:6]1.C(N(CC)CC)C.[CH2:18]([O:20][C:21](=[O:26])[CH2:22][C:23](Cl)=[O:24])[CH3:19].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:18]([O:20][C:21](=[O:26])[CH2:22][C:23]([NH:9][C:5]1([CH2:4][C:3]([O:2][CH3:1])=[O:10])[CH2:8][O:7][CH2:6]1)=[O:24])[CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 516892Sodium BicarbonateHCID 533465711105662-99-4

Product 1

HCID 59558469HCID 59558469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Amino-oxetan-3-yl)-acetic acid methyl ester (95 mg; 0.655 mmol) dissolved in CH2Cl2 (5 ml) and triethylamine (0.22 ml; 1.6 mmol) are cooled to −5° C. Chlorocarbonyl-acetic acid ethyl ester (0.1 ml; 0.79 mmol) is slowly added under stirring. The reaction mixture is warmed to room temperature, stirred for 20 minutes, poured on a saturated solution of NaHCO3 and extracted with CH2Cl2 three times. The organic phases are combined, dried over Na2SO4, filtered and evaporated to dryness. Chromatography (SiO2; Hexanes/acetone 4:1) yields the title compound as yellow resin. 1H-NMR (400 MHz; DMSO-d6): 8.93 (s, 1H); 4.54 (dd, 4H); 4.09 (q, 2H); 3.60 (s, 3H); 3.23 (s, 2H); 3.10 (s, 2H); 1.19 (t, 3H). MS (m/z) ES+: 260 (MH+)

Workup

  1. stirringstirred for 20 minutes
  2. extractionextracted with CH2Cl2 three times
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-4ace5f0f7ad441ad9c05d8e1d5582d64
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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