Tetrabutylammonium Fluoride → HCID 66653218, compound

HRID 572598Notes

Reaction equation

HRID 572598 reaction equation
[Si]([O:8][CH2:9][CH:10]([NH:39][C@@H:40]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH3:41])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])=[C:24]([C:35]([F:38])([F:37])[F:36])[CH:23]=3)[O:19][N:18]=2)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH:10]([NH:39][C@@H:40]([C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])[CH3:41])[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])=[C:24]([C:35]([F:36])([F:37])[F:38])[CH:23]=3)[O:19][N:18]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66653044HCID 66653044, compound

Product 1

HCID 66653218HCID 66653218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl N-[2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-D-alaninate (1.2 g, 0.0017 mol) in THF (25 ml) was added TBAF (50 mg, 0.1 eq) at RT. The reaction mixture was stirred at RT for 30 min and quenched with water, extracted with ethyl acetate and concentrated under reduced pressure. The crude material was purified by column chromatography using chloroform and methanol (90:10) as an eluent to afford tert-butyl N-[2-hydroxy-1-(4-{5-[2′-methyl-2-(trifluoromethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]-D-alaninate as brown oil, as mixture of two diastereomers (0.7 g, 77%). The two diastereomers were separated by chromatography (SFC on Chiralpak ADH, 20% Co-solvent: 0.5% DEA in Ethanol, Total Flow: 3 ml/min), with the first eluting isomer Rt at 4.06 min and the second eluting isomer Rt at 5.25 min.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-75e328203fb9471482f96a635a8e222a
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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