Thionyl Chloride → HCID 86738944, compound

HRID 1074541Notes

Reaction equation

HRID 1074541 reaction equation
[CH3:1][C@@:2]1(O)[C@H:9]([CH3:10])[O:8][C@@H:5]([O:6][CH3:7])[CH2:4][C@@H:3]1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14].S(Cl)(Cl)=O>C1C=CC=CC=1>[CH2:1]=[C:2]1[C@H:9]([CH3:10])[O:8][C@@H:5]([O:6][CH3:7])[CH2:4][C@@H:3]1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86737720HCID 86737720, compound

Product 1

HCID 86738944HCID 86738944, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1 g (3.7 mmol) of methyl 2,3,6-trideoxy-4-C-methyl-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (VII) in 90 ml of anhydrous benzene was treated with 2.75 ml of freshly distilled thionyl chloride and heated under reflux for 2 hours. The reaction mixture, after being cooled to room temperature, was washed with water and then treated under stirring with an aqueous solution of sodium hydrogen carbonate. The organic phase was separated off, washed with water and evaporated under vacuum to dryness to give compound (VIII), 0.82 g, 87% as a white solid; m.p. 160°-162° C., [α]D20° -180° (c=1, CHCl3). The PMR spectrum (CDCl3) showed absorptions at 1.35 (d, CH3 --C--5), 3.37 (s, CH3O), 4.37 (q, H--C--5), 4.83 (broad s, CH2 =C--4) and 4.95 δ (broad s, C--1--H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. washwas washed with water
  4. additiontreated
  5. customThe organic phase was separated off
  6. washwashed with water
  7. customevaporated under vacuum to dryness

Sources & evidence

ORD record
ord-7dc2da4c5e754ac89c2cbd48b42315fa
Source dataset
uspto-grants-1983_07
Patent number
US04393052

Reaction notes

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