Tetrabutylammonium Fluoride → HCID 57998006, compound

HRID 2425788Notes

Reaction equation

HRID 2425788 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@:14]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)([S:16][CH2:17][Si](C)(C)C)[CH2:13][C@H:12]1[C:34]([OH:36])=[O:35])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@:14]([C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)([S:16][CH3:17])[CH2:13][C@H:12]1[C:34]([OH:36])=[O:35])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57998008HCID 57998008, compound

Product 1

HCID 57998006HCID 57998006, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-1-(benzyloxycarbonyl)-4-(biphenyl-4-yl)-4-((trimethylsilyl)methylthio)pyrrolidine-2-carboxylic acid (453 mg, 0.872 mmol) in THF (10 mL) was added Tetrabutylammonium fluoride (2.61 mL, 2.61 mmol). The formed light yellow solution was stirred at room temperature overnight. Diluted with EtOAc, washed with 5% citric acid, and brine, dried over MgSO4, filtered, evaporated, to afford the desired product (2S,4R)-1-(benzyloxycarbonyl)-4-(biphenyl-4-yl)-4-(methylthio)pyrrolidine-2-carboxylic acid (390 mg, 0.784 mmol, 90% yield) as a white foam. LC-MS (retention time: 3.14 min, method B), MS m/z 448 (M+H), 400 (M-MeSH).

Workup

  1. washwashed with 5% citric acid, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6900666dc7204cffb76973476c2ebbb3
Source dataset
uspto-grants-2011_06
Patent number
US07964560B2

Reaction notes

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