Triethylamine → HCID 59049291, compound

HRID 1264471Notes

Reaction equation

HRID 1264471 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][C@H:3]1[C:6]([O:8][CH3:9])=[O:7].[C:10]([N:14]=[C:15]=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>ClCCl>[CH3:9][O:8][C:6]([C@@H:3]1[CH2:4][CH2:5][N:2]1[C:15](=[O:16])[NH:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 13246224Methyl (2S)-azetidine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 59049291HCID 59049291, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S)-Methyl azetidine-2-carboxylate hydrochloride from Reference Example 1 (185.8 mg, 1.23 mmol, 1.0 eq) was dissolved in dry dichloromethane (10.0 mL) and treated with t-butyl isocyanate (210 μL, 1.84 mmol, 1.5 eq) at about 0° C. under an argon atmosphere. After adding triethylamine (190 μL, 1.36 mmol, 1.1 eq) dropwise, the reaction mixture was warmed to about room temperature and stirred overnight. The solvent was evaporated and the residue was subjected to flash chromatography (1:1 ether:dichloromethane) to give 211.6 mg (80% yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 1.33 (s, 9H); 2.34-2.49 (m, 2H); 3.66-3.76 (m, 1H); 3.80 (s, 3H); 3.90 (q, 1H, J=8.6); 4.61 (t, 1H, J=8.6); 5.07-5.16 (br, 1H).

Workup

  1. temperaturethe reaction mixture was warmed to about room temperature
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-efe4a162eb5d4b318dcd5393ada59040
Source dataset
uspto-grants-2003_04
Patent number
US06544976B1

Reaction notes

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