Methyl chloroformate → HCID 19085814, compound

HRID 962746Notes

Reaction equation

HRID 962746 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[CH:28]=[CH:27][C:19]2OC(C(O)=O)C[O:23][C:18]=2[CH:17]=1)(=[O:15])=[O:14].C(N(CC)CC)C.Cl[C:37]([O:39][CH3:40])=O.[C:41](=O)([O-])[O-:42].[Na+].[Na+]>ClCCl>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:18](=[O:23])[C:17]23[O:42][CH2:41][CH2:40][O:39][CH:37]2[CH:19]=[CH:27][CH:28]=[C:16]3[S:13]1(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 67656924HCID 67656924, compound

Product 1

HCID 19085814HCID 19085814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 10 g of N-(4-(2-tetrahydropyranyloxy)butyl)-carboxy-1,4-benzodioxane-6-sulfonamide and 7 mL of triethylamine in 200 mL of dichloromethane cooled to 0° C. was added 2 mL of methyl chloroformate dropwise. After 3 h at 20° C., the mixture was shaken with 50 mL of saturated sodium carbonate, dried over MgSO4 and concentrated under reduced pressure. The residue was disolved in 200 mL of methanol containing 1 g of p-toluenesulfonic acid monohydrate, stirred overnight at ambient temperature, and concentrated to dryness under reduced pressure. The residue was dissolved in 200 mL of ethyl acetate, washed with 5 mL of saturated sodium carbonate, dried over MgSO4 and concentrated under reduced pressure. Trituration with ether gave 4 g of 2-(4-hydroxybutyl)-1,1-dioxido-5,6-dihydro-[1,4]dioxino[2,3-d]benzisothiazol-3(2H)-one as a white crystalline solid: mp °C.; 1H NMR (400 MHz, CDCl3): 7.4 (d, 1H), 7.25 (d, 1H), 4.5 (m, 2H), 4.4 (m, 2H), 3.8 (t, 2H), 3.7 (t, 2H), 1.95 (m, 2H), 1.7 (m, 2H), 1.55 (br s, 1H).

Workup

  1. dry with materialdried over MgSO4
  2. concentrationconcentrated under reduced pressure
  3. concentrationconcentrated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in 200 mL of ethyl acetate
  5. washwashed with 5 mL of saturated sodium carbonate
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-721ed29fdaf146a3ad6f71274d21ab16
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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