Tert-butyl 2-(butylamino)acetate → N2 (6,7-dimethoxy-2-naphthylsulfonly)-L-arginyl-N-butylglycine tert-butyl ester

HRID 1764701Notes

Reaction equation

HRID 1764701 reaction equation
[N:1]#[N:2].C(OC(=O)CN(C(=O)[C@H](CCCNC(=N)N)NS(C1C=CC2C(=CC(C)=C(C)C=2)C=1)(=O)=O)CCCC)(C)(C)C.[C:42]([O:46][C:47](=[O:54])[CH2:48][NH:49][CH2:50][CH2:51][CH2:52][CH3:53])([CH3:45])([CH3:44])[CH3:43].N#N.[CH3:57][O:58][C:59]1[CH:60]=[C:61]2[C:66](=[CH:67][C:68]=1[O:69][CH3:70])[CH:65]=[C:64]([S:71]([NH:74][C@H:75]([C:83](Cl)=[O:84])[CH2:76][CH2:77][CH2:78][NH:79][C:80](=[NH:82])[NH2:81])(=[O:73])=[O:72])[CH:63]=[CH:62]2>C(Cl)(Cl)Cl>[N:1]#[N:2].[C:42]([O:46][C:47](=[O:54])[CH2:48][N:49]([C:83](=[O:84])[C@H:75]([CH2:76][CH2:77][CH2:78][NH:79][C:80](=[NH:81])[NH2:82])[NH:74][S:71]([C:64]1[CH:63]=[CH:62][C:61]2[C:66](=[CH:67][C:68]([O:69][CH3:70])=[C:59]([O:58][CH3:57])[CH:60]=2)[CH:65]=1)(=[O:73])=[O:72])[CH2:50][CH2:51][CH2:52][CH3:53])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 22768716Tert-butyl 2-(butylamino)acetateHCID 178449150HCID 178449150, compoundHCID 178486633HCID 178486633, compound

Product 1

HCID 178449151N2 (6,7-dimethoxy-2-naphthylsulfonly)-L-arginyl-N-butylglycine tert-butyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N2 -(6,7-dimethyl-2-naphthylsulfonyl)-L-arginyl-N-butylglycine tert-butyl ester: To a stirred solution of 2.64 g of N-butylglycine tert-butyl ester in 20 ml of chloroform was carefully added N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl chloride obtained above. The reaction mixture was allowed to stand at room temperature for one hour. At the end of this period, the reaction mixture was washed twice with 20 ml of saturated sodium chloride solution and evaporated to dryness. The residue was triturated with a small amount of water to give a crystalline material. This was collected by filtration and recrystallized from ethanol-ethyl ether to give 2.28 g (82 percent) of N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-butylglycine tert-butyl ester, M.P. 164°-166° C, I.R. (KBr): 3,390, 3,165, 1,735, 1,370 cm-1.

Workup

  1. customobtained above
  2. washAt the end of this period, the reaction mixture was washed twice with 20 ml of saturated sodium chloride solution
  3. customevaporated to dryness
  4. customThe residue was triturated with a small amount of water
  5. customto give a crystalline material
  6. filtrationThis was collected by filtration
  7. customrecrystallized from ethanol-ethyl ether

Sources & evidence

ORD record
ord-17f1f4bd2d66418ebe34bb49b454d74d
Source dataset
uspto-grants-1978_09
Patent number
US04117127

Reaction notes

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