Chloride → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

HRID 1197942Notes

Reaction equation

HRID 1197942 reaction equation
Cl[CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([OH:14])=[O:13])[CH2:4]1.[CH3:15][C:16](Cl)([CH3:18])[CH3:17].[Cl-].CN1CCCC1=[O:27]>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC>[OH:27][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:16]([CH3:18])([CH3:17])[CH3:15])=[O:13])[CH2:4]1

Participants

5

Reactant 3

HCID 312ChlorideHCID 13387N-methyl-2-pyrrolidoneHCID 86747487chloride (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester

Product 1

HCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Reagents, catalysts & solvents 1

HCID 82707Tetrabutylammonium AcetateCatalyst

Conditions

Temperature
85 °C

Procedure

Solid tetrabutylammonium acetate obtained as above (111 g, 0.368 mole) was added in one portion to a mechanically stirred solution of the chloride (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester prepared in step (d) above (35 g, 0.125 mole) in HPLC grade 1-methyl-2-pyrrolidinone (504 ml) under argon. The resulting solution was stirred at 85° C. (internal temperature). After 30 to 60 minutes the reaction mixture became homogeneous and brown in color. The progress of the reaction was followed by TLC and GC analysis. (TLC: Rf=0.63 for the chloride starting material; Rf =0.54 for the title compound (silica gel, Ethyl acetate:Hexane, 1:1, visualization by Ce(SO4)2 spray). GC: Rt =7.20 minutes (starting material) and 8.66 minutes (title compound).) After 11 hours the reaction was completed.

Sources & evidence

ORD record
ord-02c9ee7d251a479997b30a754de1ef23
Source dataset
uspto-grants-1994_01
Patent number
US05278313

Reaction notes

Loading…