Furosemide → 3-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propanol

HRID 2357739Notes

Reaction equation

HRID 2357739 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:10]([Cl:21])[CH:9]=2)[O:4][CH:5]=1.Br[CH2:23][CH2:24][CH2:25][OH:26].C1CN2C(=NCCC2)C1.C(#N)C>ClCCl>[NH2:20][S:17]([C:11]1[C:10]([Cl:21])=[CH:9][C:8]([NH:7][CH2:6][C:3]2[O:4][CH:5]=[CH:1][CH:2]=2)=[C:13]([CH:12]=1)[C:14]([O:16][CH2:23][CH2:24][CH2:25][OH:26])=[O:15])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 3440Furosemide2×HCID 6342AcetonitrileHCID 123083-Bromo-1-propanolHCID 763491,5-Diazabicyclo(4.3.0)non-5-ene2×

Product 1

HCID 684556283-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of furosemide (5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid), (10) (Aldrich) (0.060 mole), 3-bromo-1-propanol (Aldrich) (0.055 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 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 3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propanol (805). See eg., T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, p. 228 (1991).

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. custommay be purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent
  8. customspin evaporated in vacuo

Sources & evidence

ORD record
ord-b816d4191b93414293dcb01bed9bf603
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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