Triethylamine → HCID 12025112, compound

HRID 2175745Notes

Reaction equation

HRID 2175745 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]>C(Cl)Cl.O>[N:1]1([C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10422AzetidineHCID 15891Phenyl chloroformate

Product 1

HCID 12025112HCID 12025112, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of azetidine (2 g, 35.08 mmol) in DCM (25 mL) were added triethylamine (14.4 mL, 105.24 mmol), followed by phenyl chloroformate (5.5 mL, 42.10 mmol) at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 16 h. Then the reaction mixture was diluted with water (30 mL) and extracted with DCM (2×50 mL). The organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was purified by column chromatography using mixture of 5% MeOH/DCM as an eluent to get the desired compound as a white solid (4.5 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 7.39-7.35 (m, 2H), 7.22-7.18 (m, 1H), 7.12-7.08 (m, 2H), 4.20-4.08 (m, 2H), 4.04-3.92 (m, 2H), 2.29-2.21 (m, 2H).

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe organic layer was washed with brine (30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was rotary evaporated under vacuum
  6. customto get residue which
  7. customwas purified by column chromatography
  8. additionmixture of 5% MeOH/DCM as an eluent

Sources & evidence

ORD record
ord-f8fe6e8ef73d4e32b1b5e64ccc7f1182
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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