M-Cresol → HCID 178495946, compound

HRID 839915Notes

Reaction equation

HRID 839915 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[N:9]#[N:10].Cl.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[CH:20]=[C:19]([S:26]([NH:29][C@H:30]([C:38]([N:40]([CH2:45][CH2:46][O:47][CH3:48])[CH2:41][C:42]([Cl:44])=[O:43])=[O:39])[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[NH:37])[NH2:36])(=[O:28])=[O:27])[CH:18]=[CH:17]2>>[N:9]#[N:10].[ClH:44].[C:2]1([CH3:8])[CH:3]=[CH:4][CH:5]=[C:6]([O:7][C:42](=[O:43])[CH2:41][N:40]([C:38](=[O:39])[C@H:30]([CH2:31][CH2:32][CH2:33][NH:34][C:35](=[NH:36])[NH2:37])[NH:29][S:26]([C:19]2[CH:18]=[CH:17][C:16]3[C:21](=[CH:22][C:23]([O:24][CH3:25])=[C:14]([O:13][CH3:12])[CH:15]=3)[CH:20]=2)(=[O:28])=[O:27])[CH2:45][CH2:46][O:47][CH3:48])[CH:1]=1

Participants

3

Reactant 2

HCID 342M-CresolHCID 178495937HCID 178495937, compound

Product 1

HCID 178495946HCID 178495946, compoundYield 86%

Conditions

Temperature
90 °C

Procedure

A mixture of 2.00 g of m-cresol and N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-(2-methoxyethyl)glycyl chloride hydrochloride obtained above was heated at 90° C for 50 minutes. At the end of this period, the reaction mixture was cooled, washed several times with dry ethyl ether, and then dissolved in 10 ml of dry ethyl alcohol. Addition of cold dry ethyl ether resulted in a precipitate which was washed several times with dry ethyl ether to give 2.12 g (86 percent) of N2 -(6,7-dimethoxy-2-naphthylsulfonyl)-L-arginyl-N-(2-methoxyethyl)glycine m-tolyl ester hydrochloride in the form of a powder. I.R. (KBr): 3,250, 3,100, 1,740, 1,640 cm-1. Various other N2 -arylsulfonyl-L-argininamides or acid addition salts thereof were synthesized in accordance with the procedures of the above examples, and the test results are summarized in Table 2.

Workup

  1. customobtained
  2. temperatureAt the end of this period, the reaction mixture was cooled
  3. washwashed several times with dry ethyl ether
  4. dissolutiondissolved in 10 ml of dry ethyl alcohol
  5. additionAddition of cold dry ethyl ether
  6. customresulted in a precipitate which
  7. washwas washed several times with dry ethyl ether

Sources & evidence

ORD record
ord-ee55c3a73e2d4cc38d3809c51ee00257
Source dataset
uspto-grants-1978_06
Patent number
US04097591

Reaction notes

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