Benzyl Bromide → benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

HRID 5420Notes

Reaction equation

HRID 5420 reaction equation
[C:1]([S:4][CH2:5][CH:6]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:19]([OH:21])=[O:20])[NH:8][C:7]1=[O:22])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O>[C:1]([S:4][CH2:5][CH:6]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:19]([O:21][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:20])[NH:8][C:7]1=[O:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 54191902HCID 54191902, compound

Product 1

HCID 53805280benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(3R)-6-(Acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (0.62 g, 1.78 mmol) is dissolved in dimethylformide (8 ml) and cesium carbonate (0.64 g, 1.96 mmol) is added, followed by benzyl bromide (0.31 g, 1.78 mmol). The mixture is stirred overnight at room temperature, poured into water (300 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layers are washed with water (2×100 ml), brine (1×200 ml), dried (MgSO4) and the solvent is evaporated. Silica gel chromatography (5% ethyl acetate/hexane) gives benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate, m.p. 192°-193° C.

Workup

  1. additionis added
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined organic layers are washed with water (2×100 ml), brine (1×200 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-2c4718ae54194d608dd1f148f41104d9
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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