Water → benzyl (3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

HRID 5421Notes

Reaction equation

HRID 5421 reaction equation
[C:1]([S:7][CH2:8][CH:9]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][S:14][CH2:13][C@@H:12]([C:22]([OH:24])=[O:23])[NH:11][C:10]1=[O:25])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C)C=O>[C:1]([S:7][CH2:8][CH:9]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][S:14][CH2:13][C@@H:12]([C:22]([O:24][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:23])[NH:11][C:10]1=[O:25])(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 54394713HCID 54394713, compound

Product 1

HCID 54261945benzyl (3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3R)-6-(Pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (0.25 g, 0.64 mmol) is dissolved in dimethylformamide (5 ml) and cesium carbonate (0.23 g, 0.71 mmol) is added, followed by benzyl bromide (0.11 g, 0.64 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 (3% ethyl acetate/hexane) gives benzyl (3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate, m.p. 135°-137° C.

Workup

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

Sources & evidence

ORD record
ord-f3916e44658846b1b722f56ff1174fcc
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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