Sodium Hydroxide → HCID 73236149, compound

HRID 2275850Notes

Reaction equation

HRID 2275850 reaction equation
[CH3:1][C:2]1([C:13]([F:16])([F:15])[F:14])[NH:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)CO1.C[Si]([C:21]#[N:22])(C)C.[C:23](=[O:26])(O)[O-].[Na+].[OH-].[Na+]>ClCCl>[F:16][C:13]([F:14])([F:15])[C:2]([NH:6][CH:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:23][OH:26])([CH3:1])[C:21]#[N:22]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium Bicarbonate2×HCID 66847496HCID 66847496, compound

Product 1

HCID 73236149HCID 73236149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 52.8 g (228.3 mmol) of 2-methyl-4-phenyl-2-(trifluoromethyl)-1,3-oxazolidine (diastereomers) Example 241A were initially charged in dichloromethane (2 l) and cooled to 0° C. 42.85 ml (342.5 mmol) of trimethylsilyl cyanide and 42.1 ml (342.5 mmol) of boron trifluoride/diethyl ether complex were added slowly and the mixture was stirred at RT for 16 h. The reaction solution was then poured into 1.5 l of saturated sodium bicarbonate solution. Another 400 g of sodium bicarbonate were then added, and the solution was adjusted to pH 10 with conc. aqueous sodium hydroxide solution. The aqueous solution was extracted three times with 500 ml of dichloromethane and the combined organic phases were dried over sodium sulphate, filtered off and concentrated. This gave 56.8 g (96% of theory, 2 diastereomers) of the target compound.

Workup

  1. extractionThe aqueous solution was extracted three times with 500 ml of dichloromethane
  2. dry with materialthe combined organic phases were dried over sodium sulphate
  3. filtrationfiltered off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f2302b3f5c4c88ab7fdd144d4d96d6
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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