Acetonitrile → HCID 59389123, compound

HRID 2357740Notes

Reaction equation

HRID 2357740 reaction equation
[NH2:1][S:2]([C:5]1[C:6]([Cl:25])=[CH:7][C:8]([NH:18][CH2:19][C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[C:9]([CH:17]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][OH:16])=[O:11])(=[O:4])=[O:3].[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27]1.C1CN2C(=NCCC2)C1.C(#N)C>ClCCl>[NH2:1][S:2]([C:5]1[C:6]([Cl:25])=[CH:7][C:8]([NH:18][CH2:19][C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[C:9]([CH:17]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:26](=[O:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:11])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7922Succinic anhydrideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 684556283-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propanol

Product 1

HCID 59389123HCID 59389123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propanol (805) (0.060 mole), succinic anhydride (Aldrich) (0.060 mole), DBN (1,5-diazabicyclo[4.3.0]non-5-ene,(Aldrich) (0.060 mole) and dry acetonitrile (50 mL) is stirred at ambient temperature for 10 hours. The reaction mixture is diluted with dichloromethane (200 mL) and extracted with 0.1 N hydrochloric acid 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 may be 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 to give 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoic acid (810).

Workup

  1. extractionextracted with 0.1 N hydrochloric acid 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. custommay be purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent
  8. customspin evaporated in vacuo
  9. customto give

Sources & evidence

ORD record
ord-c6c36e6785a64d6d9aa37f0e3b6b4b48
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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