Triethylamine → (R)-2-Methanesulfonyloxy-3-phenylpropionic acid methyl ester

HRID 7803Notes

Reaction equation

HRID 7803 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@H:4]([OH:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl.C(OCC)C>[CH3:1][O:2][C:3](=[O:13])[C@H:4]([O:12][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10986876methyl (2R)-2-hydroxy-3-phenylpropanoate

Product 1

HCID 12096286(R)-2-Methanesulfonyloxy-3-phenylpropionic acid methyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-2-hydroxy-3-phenylpropionic acid methyl ester from Step A (1.62 g, 10.9 mol) and triethylamine (3.0 mL, 21.8 mol) in dichloromethane (21.8 mL) at 0° C. was added dropwise methanesulfonyl chloride (1.28 mL, 16.4 mol). The reaction mixture was stirred at 0° C. for 1 h and was diluted with diethyl ether (200 mL) and washed with saturated ammonium chloride solution and brine. The organic layer was separated, dried with magnesium sulfate, filtered and concentrated in vacuo to give a light yellow solid 2.43 g (73%), which was used without further purification.

Workup

  1. washwashed with saturated ammonium chloride solution and brine
  2. customThe organic layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f8c307d679f4153a2cf1e3a1c6f6c09
Source dataset
uspto-grants-2006_08
Patent number
US07087622B2

Reaction notes

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