Diethyl Ether → HCID 178486631, compound

HRID 2163367Notes

Reaction equation

HRID 2163367 reaction equation
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]=[C:10]([S:17]([NH:20][C@H:21]([C:29]([OH:31])=O)[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27])(=[O:19])=[O:18])[CH:9]=[CH:8]2.P(Cl)(Cl)(Cl)(Cl)[Cl:33].CCOCC>O1CCCC1>[N:1]#[N:2].[ClH:33].[ClH:33].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]=[C:10]([S:17]([NH:20][C@H:21]([C:29]([Cl:33])=[O:31])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27])(=[O:19])=[O:18])[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24819Phosphorus pentachlorideHCID 178486646HCID 178486646, compound

Product 1

HCID 178486631HCID 178486631, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.00 g (0.00236 mole) of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginine in 20 ml of tetrahydrofuran was added little by little 0.98 g (0.0047 mole) of phosphorus pentachloride while cooling with ice water. The mixture was stirred for 1 hour at 0°-5° C., and then, for 2 hours at room temperature. To this reaction mixture was added 100 ml of dry ether, and the supernatant was removed by decantation. The residual oily product was washed with 50 ml of dry ether to give powdery N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl chloride dihydrochloride, which was added with stirring to a solution of 1.31 g (0.015 mole) of N-methyl-N-butylamine in 10 ml of chloroform. Thereafter, following the same procedures as described in Example 1, N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-N-methyl-N-butyl-L-argininamide monoacetate was obtained. Yield 0.76 g (58%).

Workup

  1. waitfor 2 hours at room temperature
  2. customthe supernatant was removed by decantation
  3. washThe residual oily product was washed with 50 ml of dry ether

Sources & evidence

ORD record
ord-d828105a891b475582ad722b047abed9
Source dataset
uspto-grants-1979_01
Patent number
US04133880

Reaction notes

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