M-Cresol → HCID 178495946, compound

HRID 1833575Notes

Reaction equation

HRID 1833575 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.

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-d5c7acd7e5dd428aa60be66964438da6
Source dataset
uspto-grants-1978_01
Patent number
US04066773

Reaction notes

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