Triethylamine → Ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate

HRID 1860058Notes

Reaction equation

HRID 1860058 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([O:27][S:2]([CH3:1])(=[O:4])=[O:3])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

Product 1

HCID 18625936Ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.94 ml) was added to a solution of ethyl 3-(4-benzyloxyphenyl)lactate (3.32 g), which is the product of Reference example 1(b), in anhydrous dichloromethane (30 ml). To this mixture triethylamine (2.47 ml) was added dropwise in an ice bath. The mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from hexane to afford the desired product (3.60 g) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-7fe5ec2ab5da42f7a3928e5fd233cdad
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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