Triethylamine → 159525-92-5

HRID 601424Notes

Reaction equation

HRID 601424 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.C(N(CC)CC)C.[S:18](Cl)([Cl:21])(=[O:20])=[O:19]>C1(C)C=CC=CC=1.ClCCl>[Cl:21][S:18]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:4]([O:3][CH3:2])=[O:10])(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 10036702159525-92-5Yield 87.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of L-proline methyl ester hydrochloride (0.33 g, 0.002 mole) in toluene (5 ml), dichloromethane (2 ml) and triethylamine (0.6 ml, 0.004 mole) was added dropwise over a period of 3 minutes to a cold (−20° C.) solution of sulfuryl chloride (0.32 ml, 0.0039 mole) in toluene. The mixture was stirred an additional 45 minutes at −20° C. The reaction was filtered and the solvent was removed under reduced pressure to give the title compound (0.40 g). 1H NMR (300 MHz, CDCl3) δ 2.13 (m, 2 H) 2.32 (m, 2 H) 3.58 (m, 1 H) 3.75 (m, 1 H) 3.79 (s, 3 H) 4.40 (dd, J=8.82, 4.04 Hz, 1 H).

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-573d516794b743f1a45bbde0ca93b9ed
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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