Methyl chloroformate → HCID 19085898, compound

HRID 962738Notes

Reaction equation

HRID 962738 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:21]([C:22](C(O)=O)=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1)(=[O:15])=[O:14].C(N(CC)CC)C.ClC(OC)=O.C(=O)(O)[O-].[Na+]>ClCCl>[O:14]=[S:13]1(=[O:15])[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:21]2[C:22](=[O:23])[N:12]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 53978174HCID 53978174, compound

Product 1

HCID 19085898HCID 19085898, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3 g of N-(4-(2-tetrahydropyranyloxy)butyl) 3-carboxycarbonylpyridine-2-sulfonamide and 2.3 mL of triethylamine in 100 mL of dichloromethane at 0° C. was added 0.8 mL of methyl chloroformate dropwise. After 2 h, the mixture was shaken with 10 mL of saturated sodium bicarbonate, dried over MgSO4 and concentrated under reduced pressure. Chromatography of the dark brown oil over silica gel, eluting with 1:1 ethyl acetate: hexane gave 3 g of homogeneous 1,1-dioxido-2-(4-(2-tetrahydropyranyloxy)butyl)-isothiazolo[5,4-b]pyridin-3(2H)-one as an amber oil.

Workup

  1. dry with materialdried over MgSO4
  2. concentrationconcentrated under reduced pressure
  3. washChromatography of the dark brown oil over silica gel, eluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-2e130360cbb149b6a160e92881e3a3ca
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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