Diethyl Ether → HCID 178476282, compound

HRID 1833528Notes

Reaction equation

HRID 1833528 reaction equation
[N:1]#[N:2].Cl.C[O:5][C:6](=[O:31])[C@H:7]([CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:30])[NH2:29])[NH:8][S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10].C(OCC)C.[CH2:37]([NH2:41])[CH2:38][CH2:39][CH3:40]>C(O)(=O)C>[N:1]#[N:2].[C:6]([OH:31])(=[O:5])[CH3:7].[CH3:23][O:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([S:9]([NH:8][C@H:7]([C:6]([NH:41][CH2:37][CH2:38][CH2:39][CH3:40])=[O:5])[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:30])[NH2:29])(=[O:11])=[O:10])[CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8007ButylamineHCID 178501459HCID 178501459, compound

Product 1

HCID 178476282HCID 178476282, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 1.0 gram amount of N2 -(6-methoxy-2-naphthalenesulfonyl)-L-arginine methyl ester hydrochloride was dissolved in 2 ml of butylamine with vigorous agitation. After the resulting solution was allowed to stand at room temperature for 2 days, the butylamine was removed in vacuo and the residual syrup was washed well with 5 ml of water to obtain a powdery product. And then this powder was dissolved in minimum volume of acetic acid. To this solution ethyl ether was added to precipitate the viscous oily product. Reprecipitation from ethanol-ethyl ether gave N2 -(6-methoxy-2-naphthalenesulfonyl)-N-butyl-L-argininamide acetate in a powder form in 74% yield.

Workup

  1. customthe butylamine was removed in vacuo
  2. washthe residual syrup was washed well with 5 ml of water
  3. customto obtain a powdery product
  4. customto precipitate the viscous oily product
  5. customReprecipitation from ethanol-ethyl ether

Sources & evidence

ORD record
ord-36bac3292bc64ace9cb3ff0da675ee54
Source dataset
uspto-grants-1978_01
Patent number
US04066759

Reaction notes

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