Oxalyl chloride → 4-(3-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoyl chloride

HRID 2357741Notes

Reaction equation

HRID 2357741 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[NH2:7][S:8]([C:11]1[C:12]([Cl:38])=[CH:13][C:14]([NH:31][CH2:32][C:33]2[O:34][CH:35]=[CH:36][CH:37]=2)=[C:15]([CH:30]=1)[C:16]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:29])[CH2:24]CC(O)=O)=[O:17])(=[O:10])=[O:9]>ClCCl>[NH2:7][S:8]([C:11]1[C:12]([Cl:38])=[CH:13][C:14]([NH:31][CH2:32][C:33]2[O:34][CH:35]=[CH:36][CH:37]=2)=[C:15]([CH:30]=1)[C:16]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:29])[CH2:24][CH2:1][C:2]([Cl:4])=[O:3])=[O:17])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 59389123HCID 59389123, compound

Product 1

HCID 866134344-(3-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of oxalyl chloride (0.040 mole) in dichloromethane (20 mL) is added dropwise to an ice bath cooled solution of 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoic acid (810) (0.040 mole) in dichloromethane (50 mL). The reaction is stirred at ambient temperature for 5 hours. The reaction solution is washed with 5% aqueous sodium bicarbonate, with water, and then with a saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to provide 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoyl chloride (813). See eg., D. L. Musso, et. al., J. Med. Chem., (2003) 46: 409.

Workup

  1. washThe reaction solution is washed with 5% aqueous sodium bicarbonate, with water
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5476f7abb7e4dacb7dda8b94fdb3161
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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