Acetonitrile → Methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate

HRID 2357752Notes

Reaction equation

HRID 2357752 reaction equation
[NH2:1][S:2]([C:5]1[C:6]([Cl:26])=[CH:7][C:8]([NH:19][CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)=[C:9]([CH:18]=1)[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])(=[O:4])=[O:3].[CH3:27][O:28][C:29](=[O:39])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37]Cl)=[O:35].C1CN2C(=NCCC2)C1.C(#N)C>ClCCl>[Cl:26][C:6]1[CH:7]=[C:8]([NH:19][CH2:20][C:21]2[O:22][CH:23]=[CH:24][CH:25]=2)[C:9]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:15])[Cl:16])=[O:11])=[CH:18][C:5]=1[S:2]([NH:1][CH2:37][O:36][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][C:29]([O:28][CH3:27])=[O:39])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 19611278Chloromethyl 6-methoxy-6-oxohexanoateHCID 593891212,2,2-Trichloroethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate

Product 1

HCID 68453359Methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,2,2-trichloroethyl 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoate (0.060 mole), chloromethyl 6-methoxy-6-oxohexanoate (0.060 mole), DBN (1,5-diazabicyclo[4.3.0]non-5-ene, Aldrich) (0.060 mole) and dry acetonitrile (100 mL) is stirred at ambient temperature for 10 hours. The reaction mixture is diluted with dichloromethane (200 mL) and extracted with sodium bicarbonate solution, washed with water, and then with a saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to give crude product, which is purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent. The fractions that contain pure product may be combined and spin evaporated in vacuo to give methyl 6-(2-chloro-4-[(2-furanylmethyl)amino]-5-(2,2,2-trichloroethoxycarbonyl)phenylsulfonamidomethoxy)(6-oxo)hexanoate.

Workup

  1. extractionextracted with sodium bicarbonate solution
  2. washwashed with water
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give crude product, which
  7. customis purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent
  8. customspin evaporated in vacuo

Sources & evidence

ORD record
ord-b1e67845653743faa1f8e0ef00f309fd
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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