Water → HCID 86737058, compound

HRID 1706842Notes

Reaction equation

HRID 1706842 reaction equation
[N:1]([CH2:4][C@H:5]1[O:12][C@H:9]([O:10][CH3:11])[CH2:8][CH2:7][C@@H:6]1[OH:13])=[N+:2]=[N-:3].[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>N1C=CC=CC=1>[N:1]([CH2:4][C@H:5]1[O:12][C@H:9]([O:10][CH3:11])[CH2:8][CH2:7][C@@H:6]1[O:13][S:15]([CH3:14])(=[O:17])=[O:16])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 86737059HCID 86737059, compound

Product 1

HCID 86737058HCID 86737058, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A cooled solution (0°) of methyl 6-azido-2,3,6-trideoxy-α-D-erythro-hexopyranoside (3 g, 16 mmol) in dry pyridine (10 ml) was treated dropwise with methanesulphonyl chloride (2.29 g, 20 mmol) with stirring for 1 h. Water (1 ml) was then added to the reaction mixture and the solvents were removed in vacuo at 30°. The residual syrup was poured into ice-water producing a precipitate which was filtered, washed with water and dried. The solid was recrystallized from benzene-petroleum ether (40°-60°) to give methyl 6-azido-4-O-methanesulphonyl-2,3,6-trideoxy-α-D-erythro-hexopyranoside (3.5 g, 83%) as a colourless solid. M.p.: 54°-56°. [α]D22 +142° (c, 1, chloroform).

Workup

  1. customthe solvents were removed in vacuo at 30°
  2. additionThe residual syrup was poured into ice-water producing a precipitate which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried
  6. customThe solid was recrystallized from benzene-petroleum ether (40°-60°)

Sources & evidence

ORD record
ord-c1297c0720d3409698ea37cc7e25be2c
Source dataset
uspto-grants-1980_06
Patent number
US04208531

Reaction notes

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