Ethylene Oxide → HCID 85082151, compound

HRID 1269095Notes

Reaction equation

HRID 1269095 reaction equation
[CH2:1]1[O:3][CH2:2]1.[CH3:4][CH:5]([CH3:31])[CH:6]([NH:18][C:19]([CH:21]1[CH2:25][CH:24]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:23][NH:22]1)=[O:20])[CH:7]1[CH:12]([OH:13])[CH:11]([OH:14])[CH:10]([OH:15])[CH:9]([S:16][CH3:17])[O:8]1>CO>[CH3:4][CH:5]([CH3:31])[CH:6]([NH:18][C:19]([CH:21]1[CH2:25][CH:24]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:23][N:22]1[CH2:1][CH2:2][OH:3])=[O:20])[CH:7]1[CH:12]([OH:13])[CH:11]([OH:14])[CH:10]([OH:15])[CH:9]([S:16][CH3:17])[O:8]1

Participants

4

Reactant 2

HCID 6354Ethylene Oxide2×HCID 78040700HCID 78040700, compound

Product 1

HCID 85082151HCID 85082151, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

Ethylene oxide (0.6 mL) was added to a solution of 4-(3-methyl-butyl)-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide (35.1 mg, 0.084 mmol), prepared as in Example 9, in methanol (3 mL), at 0° C. The reaction mixture was stirred at 4° C. overnight. Additional ethylene oxide (0.6 mL) was added and stirred at 4° C. overnight. The reaction mixture was concentrated and purified by chromatography to give the title compound as a white solid (24.1 mg, 62%).

Workup

  1. stirringstirred at 4° C. overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-91f63d316a164cadb55ef4c05af9ed75
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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