Oxalyl chloride → HCID 86613433, compound

HRID 2357734Notes

Reaction equation

HRID 2357734 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[NH2:7][S:8]([C:11]1[C:12]([Cl:35])=[CH:13][C:14]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[C:15]([CH:27]=1)[C:16]([O:18][CH2:19][CH2:20]CC(OCC)=O)=[O:17])(=[O:10])=[O:9]>ClCCl>[NH2:7][S:8]([C:11]1[C:12]([Cl:35])=[CH:13][C:14]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[C:15]([CH:27]=1)[C:16]([O:18][CH2:19][CH2:20][CH2:1][C:2]([Cl:4])=[O:3])=[O:17])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 68456450HCID 68456450, compound

Product 1

HCID 86613433HCID 86613433, compound

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-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)butanoic acid (300) (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 give 4-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)butanoyl chloride (313). 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-dba92539e9484f5e89178413e4ef585c
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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