Trifluoroacetic acid → HCID 71190250, compound

HRID 1348580Notes

Reaction equation

HRID 1348580 reaction equation
COC[O:4][C@H:5]1[C@:18]23[CH2:19][CH2:20][C@@H:7]([CH2:8][C@H:9]2[C@@:10]2([CH3:25])[C@H:15]([CH2:16][CH2:17]3)[C@:14]([CH3:24])([C:21]([OH:23])=[O:22])[CH2:13][CH2:12][CH2:11]2)[C@@H:6]1[S:26]([CH3:28])=[O:27].FC(F)(F)C(O)=O>O1CCCC1>[OH:4][C@H:5]1[C@:18]23[CH2:19][CH2:20][C@@H:7]([CH2:8][C@H:9]2[C@@:10]2([CH3:25])[C@H:15]([CH2:16][CH2:17]3)[C@:14]([CH3:24])([C:21]([OH:23])=[O:22])[CH2:13][CH2:12][CH2:11]2)[C@@H:6]1[S:26]([CH3:28])=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86594284HCID 86594284, compound

Product 1

HCID 71190250HCID 71190250, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,4S,5R,9S,10S,12S,13S,14S)-14-(methoxymethoxy)-5,9-dimethyl-13-(methylsulfinyl)tetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid (4.1 mg, 0.0099 mmol) obtained in Example 115 in tetrahydrofuran (2 mL) was added trifluoroacetic acid (2 mL) under stirring on ice. After stirring at 50° C. for 29 hours, the reaction mixture was evaporated, to give (1R,4S,5R,9S,10S,12S,13S,14S)-14-hydroxy-5,9-dimethyl-13-(methylsulfinyl)tetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylic acid. This product was further purified by silica gel column chromatography so as to separate two isomers based on the configuration of sulfoxide, to give isomer 1 (0.71 mg) and isomer 2 (1.01 mg).

Workup

  1. stirringAfter stirring at 50° C. for 29 hours
  2. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-3dec72ac08ae4fb8a5a5c8241a86b9d1
Source dataset
uspto-grants-2007_05
Patent number
US07211589B2

Reaction notes

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