4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → HCID 89533471, compound

HRID 1466173Notes

Reaction equation

HRID 1466173 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:12](=[O:21])[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C:15]1=[O:20].[CH3:22][C:23]1[C:31]2[CH2:30][O:29][C:28](=[O:32])[C:27]=2[CH:26]=[CH:25][C:24]=1[C@@H:33]1[CH2:35][O:34]1>CCO>[OH:34][C@H:33]([C:24]1[CH:25]=[CH:26][C:27]2[C:28](=[O:32])[O:29][CH2:30][C:31]=2[C:23]=1[CH3:22])[CH2:35][N:17]1[CH2:18][CH2:19][N:14]([CH2:13][C:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])=[O:21])[C:15](=[O:20])[CH2:16]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-oneHCID 89524963HCID 89524963, compound

Product 1

HCID 89533471HCID 89533471, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)-2-oxoethyl]piperazin-2-one (30 mg, 0.10 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (40 mg, 0.21 mmol) in EtOH (2 mL) was heated to 140° C. in a microwave tube for 1 hour. The solution was concentrated to dryness, re-dissolved in MeOH, filtered and shot into Mass-directed HPLC for separation to give the title product. LC-MS (IE, m/z): 479 [M+1]+.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. dissolutionre-dissolved in MeOH
  3. filtrationfiltered
  4. customshot into Mass-directed HPLC for separation

Sources & evidence

ORD record
ord-cd8b042a135945f1bc21d95a2dc31609
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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