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

HRID 21973Notes

Reaction equation

HRID 21973 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-azacyclodecane-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-abe1e0ccdf9f42868f0a36b7ee46d87d
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Reaction notes

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