Methanesulfonyl chloride → HCID 86735301, compound

HRID 461932Notes

Reaction equation

HRID 461932 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([NH:12][C:13]([C:15]1[S:19][C:18]([O:20][CH2:21][CH:22]([OH:25])[CH2:23][OH:24])=[N:17][CH:16]=1)=[O:14])[CH2:7][CH2:8][CH2:9][C:10]#[CH:11]>N1C=CC=CC=1>[OH:25][CH:22]([CH2:21][O:20][C:18]1[S:19][C:15]([C:13]([NH:12][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11])=[O:14])=[CH:16][N:17]=1)[CH2:23][O:24][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 21392658HCID 21392658, compound

Product 1

HCID 86735301HCID 86735301, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In this example 0.42 g. of methanesulfonyl chloride is added with rapid stirring to a mixture containing 1.2 g. of (+) 3-[5-(hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propane-1,2-diol in 20 ml. of pyridine at -30° C. The mixture is then allowed to warm to room temperature and evaporated to dryness affording a residue of (+) 2-hydroxy-1-methylsulfonyloxy-3-(5(-hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propane. The residue is then dissolved in 50 ml. of anhydrous methanol and cooled to 0° C. A mixture containing 1 g. of sodium methoxide in 10 ml. of anhydrous methanol is added and the resulting mixture stirred for 2 minutes and then evaporated to remove methanol. 100 Ml. of ethyl acetate is added and the resulting ethyl acetate mixture washed three times with water, dried over magnesium sulfate, and evaporated affording a residue of (+) 1,2-epoxy-3-[5-(hex-5-ynylaminocarbonyl)thiazol-2-yloxy]propane.

Workup

  1. additioncontaining 1.2 g
  2. customat -30° C
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-3bcd6f66b0584d50b3ade5579c2c7d55
Source dataset
uspto-grants-1977_12
Patent number
US04064257

Reaction notes

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