Tetrabutylammonium Fluoride → HCID 67741564, compound

HRID 1901686Notes

Reaction equation

HRID 1901686 reaction equation
[Si]([O:8][CH2:9][C@H:10]([N:12]1[CH2:16][C@@H:15]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[O:14][C:13]1=[O:26])[CH3:11])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][CH2:17][C@H:15]1[O:14][C:13](=[O:26])[N:12]([C@H:10]([CH3:11])[CH2:9][OH:8])[CH2:16]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53837597HCID 53837597, compound

Product 1

HCID 67741564HCID 67741564, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation was repeated, except that 0.88 g of 3-(2-t-butyldimethylsilyloxy-1(R)-methylethyl)-5(S)-(3-chlorophenoxymethyl)oxazolidin-2-one (prepared as described in Preparation 27), 6.6 ml of tetrabutylammonium fluoride (26% w/v in tetrahydrofuran) and 10 ml of anhydrous tetrahydrofuran were used, to give 0.58 g of the title compound having an Rf value of 0.45 (on silica gel thin layer chromatography, using ethyl acetate as the developing solvent) and having [α]D =+45.6° (methanol, c=1.000).

Workup

  1. customA procedure similar to that described in Preparation

Sources & evidence

ORD record
ord-9e0f8c1739fd49258a4cc402304c8e3c
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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