Methyl iodide → Trifluoroacetic acid

HRID 1931554Notes

Reaction equation

HRID 1931554 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[NH2:8][C@:9]([CH3:60])([C:56]([CH3:59])([CH3:58])[CH3:57])[CH2:10][O:11][C@@H:12]1[C@@:19]2([CH3:44])[C@@H:20]3[CH2:21][CH2:22][C@H:23]4[C:32]([C@@:15]3([CH2:16][O:17][CH2:18]2)[CH2:14][C@H:13]1[N:45]1[C:49](C2C=CN=CC=2)=[N:48][CH:47]=[N:46]1)=[CH:31][CH2:30][C@:29]1([CH3:33])[C@:24]4([CH3:43])[CH2:25][CH2:26][C@@:27]([C@H:38]([CH3:42])[CH:39]([CH3:41])[CH3:40])([CH3:37])[C@H:28]1[C:34]([OH:36])=[O:35].CI>CN(C)C=O>[F:5][C:4]([F:7])([F:6])[C:2]([O-:3])=[O:1].[NH2:8][C@:9]([CH3:60])([C:56]([CH3:59])([CH3:57])[CH3:58])[CH2:10][O:11][C@@H:12]1[C@@:19]2([CH3:44])[C@@H:20]3[CH2:21][CH2:22][C@H:23]4[C:32]([C@@:15]3([CH2:16][O:17][CH2:18]2)[CH2:14][C@H:13]1[N:45]1[C:49]([CH:4]2[CH:2]=[CH2+:19][CH:12]=[CH:13][N:45]2[CH3:49])=[N:48][CH:47]=[N:46]1)=[CH:31][CH2:30][C@:29]1([CH3:33])[C@:24]4([CH3:43])[CH2:25][CH2:26][C@@:27]([C@H:38]([CH3:42])[CH:39]([CH3:41])[CH3:40])([CH3:37])[C@H:28]1[C:34]([OH:36])=[O:35].[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 131729740HCID 131729740, compound

Product 1

HCID 6422Trifluoroacetic acidYield 1,823.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-15-[[(2R)-2-amino-2,3,3-trimethylbutyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-14-[5-(4-pyridinyl)-1H-1,2,4-triazol-1-yl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid-TFA salt (Example 173, 50 mg, 0.059 mmol) and methyl iodide (0.1 mL, 1.6 mmol) in dimethylformamide (0.2 mL) was blanketed with nitrogen and stirred at room temperature for 2.5 hours. The mixture was evaporated and purified by reverse phase HPLC using a 19×150 mm Sunfire Preparative C18 OBD column (elution with MeCN/water+0.05% TFA). Fractions were evaporated and freeze-dried from a mixture of ethanol and benzene to give the title compound as a TFA salt (40.9 mg).

Workup

  1. customThe mixture was evaporated
  2. custompurified by reverse phase HPLC
  3. washC18 OBD column (elution with MeCN/water+0.05% TFA)
  4. customFractions were evaporated
  5. dry with materialfreeze-dried from a mixture of ethanol and benzene

Sources & evidence

ORD record
ord-dce0b03aeb89412eb43c9040f215c429
Source dataset
uspto-grants-2012_05
Patent number
US08188085B2

Reaction notes

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