Ethanol → HCID 178449153, compound

HRID 616182Notes

Reaction equation

HRID 616182 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].S(Cl)([Cl:38])=O.[CH2:40](O)[CH3:41]>>[N:1]#[N:2].[ClH:38].[CH2:40]([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])[CH3:41]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 178449157HCID 178449157, compound

Product 1

HCID 178449153HCID 178449153, compoundYield 90%

Procedure

To an ice-cooled suspension of 1.0 g of N2 -(2-naphthalenesulfonyl)-L-arginyl-N-butylglycine in 15 ml of ethanol was added dropwise 0.5 ml of thionyl chloride with vigorous stirring. The reaction mixture was allowed to stand for 2 hours at room temperature and then refluxed for 2 hours. At the end of this period, the reaction mixture was evaporated to dryness, and the residual syrup was treated with cold ethyl ether to give 1.02 g (90%) of N2 -(2-naphthalenesulfonyl)-L-arginyl-N-butylglycine ethyl ester hydrochloride in the form of a powder.

Workup

  1. temperaturerefluxed for 2 hours
  2. customAt the end of this period, the reaction mixture was evaporated to dryness
  3. additionthe residual syrup was treated with cold ethyl ether

Sources & evidence

ORD record
ord-31132c42a0fd482cafc5a6621aa9e049
Source dataset
uspto-grants-1978_02
Patent number
US04072744

Reaction notes

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