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

HRID 1268960Notes

Reaction equation

HRID 1268960 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22][S:24]([CH3:23])(=[O:26])=[O:25])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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

To a solution of ethyl 3-(4-benzyloxyphenyl)lactate (3.32 g) obtained from Reference example 24(a) in anhydrous dichloromethane (30 ml) was added methanesulfonyl chloride (0.94 ml), and then triethylamine (2.47 ml) was added dropwise thereto in an ice bath. The reaction solution was stirred for 3 hours at room temperature and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, and the separated ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from hexane to afford the target compound (3.60 g) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialthe separated ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-e5be4514111348399411fa8d41078fdb
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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