N-(2-ethylthioethyl)-glycine tert-butyl ester → HCID 178477443, compound

HRID 1834875Notes

Reaction equation

HRID 1834875 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][NH:8][CH2:9][CH2:10][S:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[N:15]#[N:16].Cl.[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][C:29]=1[O:30][CH3:31])[CH:26]=[C:25]([S:32]([NH:35][C@H:36]([C:44](Cl)=[O:45])[CH2:37][CH2:38][CH2:39][NH:40][C:41](=[NH:43])[NH2:42])(=[O:34])=[O:33])[CH:24]=[CH:23]2>C(Cl)(Cl)Cl>[N:15]#[N:16].[C:1]([O:5][C:6](=[O:14])[CH2:7][N:8]([C:44](=[O:45])[C@H:36]([CH2:37][CH2:38][CH2:39][NH:40][C:41](=[NH:42])[NH2:43])[NH:35][S:32]([C:25]1[CH:24]=[CH:23][C:22]2[C:27](=[CH:28][C:29]([O:30][CH3:31])=[C:20]([O:19][CH3:18])[CH:21]=2)[CH:26]=1)(=[O:34])=[O:33])[CH2:9][CH2:10][S:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 20372345N-(2-ethylthioethyl)-glycine tert-butyl esterHCID 178486632HCID 178486632, compound

Product 1

HCID 178477443HCID 178477443, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4.80 g of N-(2-ethylthioethyl)-glycine tert-butyl ester in 40 ml of chloroform was carefully added N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl chloride hydrochloride obtained above. The reaction mixture was allowed to stand at room temperature overnight. 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 powder. This was collected by filtration and reprecipitated with ethanol-diethyl ether to give 5.00 g of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-(2-ethylthioethyl)glycine tert-butyl ester.

Workup

  1. customobtained above
  2. washThe 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 powder
  6. filtrationThis was collected by filtration
  7. customreprecipitated with ethanol-diethyl ether

Sources & evidence

ORD record
ord-071703dfd5f84a618b37b54da9ef0cd9
Source dataset
uspto-grants-1978_01
Patent number
US04071621

Reaction notes

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