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

HRID 1197945노트

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HRID 1197945 반응식
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)C1C=CC=CC=1.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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 10981353Tetrabutylammonium Benzoate촉매

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온도
100 °C

실험 절차

Solid tetrabutylammonium benzoate obtained as above (126.47 g, 0.348 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 as in step (d) of Example 1 above (32.3 g, 0.116 mole) in HPLC grade 1-methyl-2-pyrrolidinone (465 ml) under argon. The resulting solution was stirred at 100° 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 =0.47 for the chloride starting material; Rf =0.35 for the title compound (silica gel, Ether: Hexane, 4:6, visualization by Ce(SO4)2 spray). After 6.5 hours the reaction was completed.

출처 및 근거

ORD 기록
ord-b58a773ce46942d49b44e3f164b8ed53
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278313

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