p-Toluenesulfonic acid monohydrate → HCID 178449145, compound

HRID 616183Notes

Reaction equation

HRID 616183 reaction equation
[N:1]#[N:2].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([NH:16][C@H:17]([C:25]([N:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][C:29]([OH:31])=[O:30])=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23])(=[O:15])=[O:14].O.[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43]([OH:46])(=[O:45])=[O:44])=[CH:39][CH:38]=1>C(O)C1C=CC=CC=1.C1C=CC=CC=1>[N:1]#[N:2].[C:37]1([CH3:47])[CH:38]=[CH:39][C:40]([S:43]([OH:46])(=[O:44])=[O:45])=[CH:41][CH:42]=1.[CH2:47]([O:30][C:29](=[O:31])[CH2:28][N:27]([C:25](=[O:26])[C@H:17]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:23])[NH2:24])[NH:16][S:13]([C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1)(=[O:14])=[O:15])[CH2:32][CH2:33][CH2:34][CH3:35])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178449157HCID 178449157, compound

Product 1

HCID 178449145HCID 178449145, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 244Benzyl AlcoholSolvent

Procedure

A mixture of 1.2 g of N2 -(2-naphthalenesulfonyl)-L-arginyl-N-butylglycine and 1.0 g of p-toluenesulfonic acid monohydrate in 5 ml of benzyl alcohol and 30 ml of benzene was refluxed for 5 hours, while removing water by azeotropic distillation. At the end of this period, the solvent was evaporated and then 100 ml of ethyl ether was added to the residue to give 1.73 g (93%) of N2 -(2-naphthalenesulfonyl) L-arginyl-N-butylglycine benzyl ester p-toluenesulfonate in the form of a powder.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customwhile removing water
  3. distillationby azeotropic distillation
  4. customAt the end of this period, the solvent was evaporated
  5. addition100 ml of ethyl ether was added to the residue

Sources & evidence

ORD record
ord-35d450f2992d43b8a17a397a72fc53b6
Source dataset
uspto-grants-1978_02
Patent number
US04072744

Reaction notes

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