Triethylamine → Ethyl (alphaR)-alpha-[(methylsulfonyl)oxy]benzenebutanoate

HRID 278461

Reaction equation

HRID 278461 reaction equation
C(N(CC)CC)C.[OH:8][C@H:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:8][C@H:9]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733848Ethyl (R)-2-hydroxy-4-phenylbutyrate

Product 1

HCID 14794470Ethyl (alphaR)-alpha-[(methylsulfonyl)oxy]benzenebutanoateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (583 mg) was added dropwise to a stirred mixture of ethyl (R)-2-hydroxy-4-phenylbutyrate (1.0 g) and methanesulfonyl chloride (660 mg) in dichloromethane (10 ml) at ice-bath temperature. After 40 minutes, the reaction mixture was partitioned between dichloromethane and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give ethyl (R)-2-methylsulfonyloxy-4-phenylbutyrate (1.37 g) as an oil. This material was used immediately without further purification. NaH (60% in mineral oil, 192 mg) was added to a solution of 4-imidazolecarboxamide (534 mg) in DMF (8 ml) at room temperature. The reaction mixture was stirred for 30 minutes. The methanesulfonate prepared above was added and the resulting mixture was stirred for 3 hours at 60° C.

Workup

  1. customthe reaction mixture was partitioned between dichloromethane and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8533e20906c04d8ca834359ae849788c
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Linked notes

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