Benzyl Bromide → trans Benzyl 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecane-10-carboxylate

HRID 5401

Reaction equation

HRID 5401 reaction equation
[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([OH:18])=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([O:18][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 86747202trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

Product 1

HCID 131718122trans Benzyl 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecane-10-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.15 g, 0.52 mmol) is dissolved in dimethylformamide (2.5 mL). Benzyl bromide (0.062 mL, 0.52 mmol) and cesium carbonate (0.085 g, 0.26 mmol) are added, and the reaction is stirred at room temperature overnight. The reaction is diluted with water, and the aqueous layer is extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give trans benzyl 3-(acetylthiomethyl)-2-oxo-1-aza-cyclodecane-10-carboxylate m.p. 117°-118° C.

Workup

  1. extractionthe aqueous layer is extracted several times with methylene chloride
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. customthe solvent is evaporated
  4. customThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ee7debe1bbd340b6a45aa36abc48f31c
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Linked notes

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