Diethyl Ether → HCID 178476283, compound

HRID 2072184Notes

Reaction equation

HRID 2072184 reaction equation
[N:1]#[N:2].Cl.C[O:5][C:6](=[O:29])[C@H:7]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27])[NH:8][S:9]([C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10].C(O[CH2:33][CH3:34])C.CO[CH2:37][CH2:38][NH2:39]>C(O)(=O)C>[N:1]#[N:2].[C:6]([OH:29])(=[O:5])[CH3:7].[C:12]1([S:9]([NH:8][C@H:7]([C:6]([NH:39][CH2:38][CH2:37][CH2:33][CH3:34])=[O:29])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27])(=[O:10])=[O:11])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 80182-MethoxyethylamineHCID 178501460HCID 178501460, compound

Product 1

HCID 178476283HCID 178476283, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 1.0 gram amount of N2 -(1-naphthalenesulfonyl)-L-arginine methyl ester hydrochloride was dissolved in 2 ml of methoxyethylamine with vigorous agitation. After the resulting solution was allowed to stand at room temperature for 2 days, the methoxyethylamine 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 -(1-naphthalenesulfonyl)-N-butyl-L-argininamide acetate in a powder form in 77% yield.

Workup

  1. customthe methoxyethylamine 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-b1db806771cf4d35bbcc4f079520ad19
Source dataset
uspto-grants-1977_09
Patent number
US04049645

Reaction notes

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