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

HRID 866890Notes

Reaction equation

HRID 866890 reaction equation
[C:1]([O:5][C:6](=[O:13])[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[N:14]#[N:15].[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH:24]=[C:23]([S:30]([NH:33][C@H:34]([C:42](Cl)=[O:43])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:41])[NH2:40])(=[O:32])=[O:31])[CH:22]=[CH:21]2>C(Cl)(Cl)Cl>[N:14]#[N:15].[C:1]([O:5][C:6](=[O:13])[CH2:7][N:8]([C:42](=[O:43])[C@H:34]([CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:40])[NH2:41])[NH:33][S:30]([C:23]1[CH:22]=[CH:21][C:20]2[C:25](=[CH:26][C:27]([O:28][CH3:29])=[C:18]([O:17][CH3:16])[CH:19]=2)[CH:24]=1)(=[O:32])=[O:31])[CH2:9][CH2:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 22768716Tert-butyl 2-(butylamino)acetateHCID 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

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-861304b10ad4411784ec406488a3f4dd
Source dataset
uspto-grants-1978_07
Patent number
US04101653

Reaction notes

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