Ethylene Oxide → HCID 85109891, compound

HRID 1269096Notes

Reaction equation

HRID 1269096 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]([F:30])[F: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]([F:30])[F: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 72748139HCID 72748139, compound

Product 1

HCID 85109891HCID 85109891, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

Ethylene oxide (0.4 mL) was added to a solution of 4-(3,3-difluoro-propyl)-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide, prepared as in Example 14 (29.7 mg, 0.07 mmol), in methanol (2 mL), at 0° C. The reaction mixture was stirred at 4° C. overnight. Additional ethylene oxide (0.4 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 (19.3 mg, 59%).

Workup

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

Sources & evidence

ORD record
ord-92f1273a8711441c8413b5f509d56711
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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