Benzyl Bromide → HCID 22719690, compound

HRID 1582054Notes

Reaction equation

HRID 1582054 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([O:9][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 130175572-[(Acetylthio)methyl]-4-methylpentanoic acid

Product 1

HCID 22719690HCID 22719690, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-acetylthio-2-isobutylpropionic acid [obtained by Michael addition of thiolacetic acid onto 2-isobutylacrylic acid] (7 g, 34.3 mmol), benzyl bromide (4.29 ml, 36 mmol) and DBU (5.2 ml, 35 mmol) in toluene (55 ml) was stirred for 18 hours at room temperature. The solvents were evaporated in vacuo. The residue was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic layer was washed with brine and dried over MgSO4. Purification of the residue by chromatography on silica gel (eluant: dichloromethane-ether (9:1)) gave benzyl 3-acetylthio-2-isobutylpropionate (8.4 g).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and 5% sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customPurification of the residue by chromatography on silica gel (eluant: dichloromethane-ether (9:1))

Sources & evidence

ORD record
ord-2fe8fb52a3f14f6590627fcd30de8e42
Source dataset
uspto-grants-2004_05
Patent number
US06734184B1

Reaction notes

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