Dimethylformamide → HCID 10136163, compound

HRID 585498Notes

Reaction equation

HRID 585498 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][N:12]([S:17]([CH2:20][CH:21]([CH:25]([CH3:27])[CH3:26])C(O)=O)(=[O:19])=[O:18])[CH2:11][CH2:10]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=[O:30].C[N:35](C)[CH:36]=[O:37]>ClCCl>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][N:12]([S:17]([CH2:20][CH:21]([CH:25]([CH3:27])[CH3:26])[C:36]([NH:35][OH:30])=[O:37])(=[O:19])=[O:18])[CH2:11][CH2:10]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10157415HCID 10157415, compound

Product 1

HCID 10136163HCID 10136163, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(6-Cyclohexyl-3,4-dihydro-1H-isoquinoline-2-sulfonylmethyl)-3-methyl-butyric acid (143 mg) was dissolved in dichloromethane (15 ml) under a nitrogen atmosphere and oxalyl chloride (0.15 ml) added, followed by a solution of 10% N,N-dimethylformamide in dichloromethane (7 drops). The reaction was stirred at room temperature for 2 h then evaporated under reduced pressure and azeotroped with 1:1 dichloromethane-hexane (2×10 ml). The residue was dried under vacuum then suspended in tetrahydrofuran (15 ml) and treated with 50% wt solution of aqueous hydroxylamine (0.7 ml). The mixture was left to stir at room temperature for 1 h then evaporated under reduced pressure. The residue was triturated with water (20 ml) and the resulting solid filtered off, washed with water (10 ml) and dried under vacuum at 40° C. to give the title compound (120 mg, 82%).

Workup

  1. customthen evaporated under reduced pressure
  2. customazeotroped with 1:1 dichloromethane-hexane (2×10 ml)
  3. customThe residue was dried under vacuum
  4. additiontreated with 50% wt solution of aqueous hydroxylamine (0.7 ml)
  5. waitThe mixture was left
  6. stirringto stir at room temperature for 1 h
  7. customthen evaporated under reduced pressure
  8. customThe residue was triturated with water (20 ml)
  9. filtrationthe resulting solid filtered off
  10. washwashed with water (10 ml)
  11. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-d567d55747834e24914e7babb4048620
Source dataset
uspto-grants-2005_08
Patent number
US06933306B2

Reaction notes

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