Triethylamine → HCID 86601487, compound

HRID 270116Notes

Reaction equation

HRID 270116 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[N+](C1C=C(S(O[CH2:26][C@:27]2([CH3:30])[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O.C(N(CC)CC)C>ClCCl>[CH3:26][C@@:27]1([CH2:30][O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:29][O:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 86597620HCID 86597620, compound

Product 1

HCID 86601487HCID 86601487, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-hydroxypthalimide (5.3 g, 32.5 mmol), [(2S)-2-methyloxiran-2-yl]methyl 3-nitrobenzenesulfonate (5.9 g, 21.6 mmol) and triethylamine (10.6 ml) in dichloromethane (15 ml) was stirred under nitrogen at ambient temperature for 24 h. The reaction mixture was poured onto a silica column and eluted with dichloromethane to give the sub-title compound as a colourless solid (3.1 g).

Workup

  1. additionThe reaction mixture was poured onto a silica column
  2. washeluted with dichloromethane

Sources & evidence

ORD record
ord-c6e78bb1857e4652883bb92d5f0b3d3d
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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