Triethylamine → HCID 86750888, compound

HRID 1781537Notes

Reaction equation

HRID 1781537 reaction equation
COCCOC[O:7][C:8]1[C:16]([CH2:17]/[CH:18]=[C:19](\[CH3:28])/[CH2:20][CH:21]([NH2:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]([O:29][CH3:30])[C:14]([CH3:31])=[C:13]2[C:9]=1[C:10](=[O:32])[O:11][CH2:12]2.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[OH:7][C:8]1[C:16]([CH2:17]/[CH:18]=[C:19](\[CH3:28])/[CH2:20][CH:21]([NH:27][S:41]([CH3:40])(=[O:43])=[O:42])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:15]([O:29][CH3:30])[C:14]([CH3:31])=[C:13]2[C:9]=1[C:10](=[O:32])[O:11][CH2:12]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131720026HCID 131720026, compound

Product 1

HCID 86750888HCID 86750888, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl (E)-6-(4-methoxyethoxymethoxy-1,3-dihydro-6-methoxy-7-methyl -3-oxoisobenzofuran-5-yl)-2-amino-4-methyl-4-hexenoate (373 mg) was dissolved in CH2Cl2 (10 ml), cooled to 0° C., and triethylamine (0.17 ml) and methylsulfonyl chloride (0.09 ml) were added. The mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours. The reaction mixture was diluted with CH2Cl2 (10 ml), washed with water (10 ml), dried over Na2SO4, and evaporated to dryness to give a residue which was passed through a column (silica gel, hexanes-EtOAc 1:1) giving 368 mg (82%) of ethyl (E)-6-(4-hydroxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5yl) -2-methylsulfonylamino-4-methyl-4-hexenoate as a colorless oil.

Workup

  1. washwashed with water (10 ml)
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customto give a residue which

Sources & evidence

ORD record
ord-2f7d3cefcf884ad1aca8cee6ff44c882
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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