Water → HCID 136364555, compound

HRID 2351855Notes

Reaction equation

HRID 2351855 reaction equation
[OH:1][CH2:2][C:3]1[C:11]2[CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:8]([CH3:26])[NH:7][C:6]=2[S:5][N:4]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>O1CCCC1>[CH3:34][S:35]([O:1][CH2:2][C:3]1[C:11]2[CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:8]([CH3:26])[NH:7][C:6]=2[S:5][N:4]=1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136364556HCID 136364556, compound

Product 1

HCID 136364555HCID 136364555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an argon stream, 630 mg (1.68 mM) of ethyl 3-hydroxymethyl-6-methyl-4-(3-nitrophenyl)-4,7-dihydroisothiazolo[5,4-b]pyridine-5-carboxylate obtained in Example 2 was dissolved in 6 ml of anhydrous tetrahydrofuran, and under ice cooling, 0.62 ml (4.45 mM) of triethylamine was added. A solution of 0.26 ml (3.36 mM) of methanesulfonyl chloride in 2 ml of anhydrous tetrahydrofuran was added dropwise, and reacted at the above temperature for 45 minutes. Water (6 ml) was added to the reaction mixture, and the mixture was stirred for 10 minutes. The mixture was then poured into 10% HCl-ice, and extracted with methylene chloride. The methylene chloride layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 927 mg of crude ethyl 3-methanesulfonyloxymethyl-6-methyl-4-(3-nitrophenyl)-4,7-dihydroisothiazolo[5,4-b]pyridine-5-carboxylate as a pale yellow jelly-like product.

Workup

  1. customreacted at the above temperature for 45 minutes
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c194f374211644158925a3dcb2a66263
Source dataset
uspto-grants-1989_10
Patent number
US04874760

Reaction notes

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