Triethylamine → HCID 16307882, compound

HRID 1776184Notes

Reaction equation

HRID 1776184 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[CH3:7][O:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][S:2]([N:11]1[CH2:12][CH2:13][CH2:14][CH:10]1[C:9]([O:8][CH3:7])=[O:15])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 16307882HCID 16307882, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (2.3 mL, 30 mmol) was slowly added to a stirring solution of D/L-proline methyl ester hydrochloride (5.0 g, 30.2 mmol) and triethylamine (8.4 mL, 60 mmol) in anhydrous methylene chloride (75 mL). The reaction was stirred overnight at ambient temperature and then diluted with ethyl acetate. The organic layer was successively washed with water, 1N aqueous hydrochloric acid twice, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate), and filtered. The solution was concentrated under reduced pressure to give the desired product as a tan liquid (4.45 g, 72%). 1H NMR (CDCl3, 300 MHz) δ 4.53-4.49 (dd, 1H, J=8.7, 3.6 Hz), 3.75 (s, 3H), 3.57-3.54 (m, 1H), 3.52-3.42 (m, 1H), 3.01 (s, 3H), 2.32-2.22 (m, 1H), 2.11-1.98 (m, 3H).

Workup

  1. washThe organic layer was successively washed with water, 1N aqueous hydrochloric acid twice
  2. dry with materialsaturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ca6a02d53b5f41ad919d1a97fcbca728
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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