Tetrabutylammonium Fluoride → HCID 86752100, compound

HRID 863265Notes

Reaction equation

HRID 863265 reaction equation
[CH2:1]([NH:5][C:6](=[O:40])[C@H:7]([CH3:39])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:10]1[CH2:23][C@H:24]([CH3:38])[CH2:25][CH2:26][O:27][Si](C(C)C)(C(C)C)C(C)C)[CH2:2][CH2:3][CH3:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([NH:5][C:6](=[O:40])[C@H:7]([CH3:39])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@H:10]1[CH2:23][C@H:24]([CH3:38])[CH2:25][CH2:26][OH:27])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86752101HCID 86752101, compound

Product 1

HCID 86752100HCID 86752100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

475 mg of 3-[N-tert-butoxycarbonyl-4(S)-[4-triisopropylsilyloxy-2(S)-methylbutyl]-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide, dissolved in 12 ml of tetrahydrofuran, are stirred together with 1.63 ml of a 1M tetrabutylammonium fluoride solution in tetrahydrofuran at room temperature for 3 h. The organic phase is washed with saturated sodium chloride solution, added over sodium sulfate and concentrated. The crude product is purified by FC over 50 g of silica gel (mobile phase H). The title compound is obtained as the pure diastereomer: Rf (H)=0.48.

Workup

  1. washThe organic phase is washed with saturated sodium chloride solution
  2. additionadded over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified by FC over 50 g of silica gel (mobile phase H)

Sources & evidence

ORD record
ord-020638e22db2418bb46fe3a9d2206908
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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