HCID 68957620, compound → 4-(Acetylamino)-3-{[(2S)-2-methyloxiran-2-yl]methoxy}phenyl benzoate

HRID 270070Notes

Reaction equation

HRID 270070 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:12]([OH:20])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=C(S(O[CH2:34][C@:35]2([CH3:38])[CH2:37][O:36]2)(=O)=O)C=CC=1)([O-])=O>CN1CCCC1=O>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:12]([O:20][CH2:34][C@:35]2([CH3:38])[CH2:37][O:36]2)[CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68957620HCID 68957620, compoundHCID 86597620HCID 86597620, compound

Product 1

HCID 866014794-(Acetylamino)-3-{[(2S)-2-methyloxiran-2-yl]methoxy}phenyl benzoateYield 39%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

This compound was prepared from 4-(acetylamino)-3-hydroxyphenyl benzoate (2.71 g, 10 mmol) and [(2S)-2-methyloxiran-2-yl]methyl 3-nitrobenzenesulfonate using the standard procedure and 1-methylpyrrolidin-2-one as a solvent. Flash chromatography on silica gel (ethyl acetate/n-heptane) afforded the subtitled compound as a colourless solid (1.31 g, 3.9 mmol, 39%).

Sources & evidence

ORD record
ord-5c40fa6ce3cf4fc0ba9c3efa236767a1
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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