Isopropanol → HCID 178459595, compound

HRID 651978Notes

Reaction equation

HRID 651978 reaction equation
[N:1]#[N:2].[S:3]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:27])[NH2:26])([C:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:11]([N:12]([CH3:14])[CH3:13])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].S(Cl)([Cl:33])=O.[CH:35](O)([CH3:37])[CH3:36]>>[N:1]#[N:2].[ClH:33].[ClH:33].[CH:35]([O:29][C:28](=[O:30])[C@H:20]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:26])[NH2:27])[NH:19][S:3]([C:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:11]([N:12]([CH3:13])[CH3:14])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:5])([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 178482655HCID 178482655, compound

Product 1

HCID 178459595HCID 178459595, compoundYield 90%

Procedure

To an ice-cooled suspension of 1.0 gram of N2 -dansyl-L-arginine in 15 ml of isopropanol was added dropwise 0.5 ml of thionyl chloride with vigorous stirring. After being allowed to stand for 2 hours at room temperature, the reaction mixture was refluxed for 4 hours, and was evaporated to dryness (syrup). Treatment of the residual syrup with cold ethyl ether gave crude crystals. After recrystallization from isopropanol-ethyl ether, colorless N2 -dansyl-L-arginine isopropyl ester dihydrochloride was obtained in 90% yield; mp. 110°-120° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 hours
  2. customwas evaporated to dryness (syrup)
  3. customTreatment of the residual syrup with cold ethyl ether gave crude crystals
  4. customAfter recrystallization from isopropanol-ethyl ether

Sources & evidence

ORD record
ord-2f3732b9e6c04f93a3adcaa34f8a5cb5
Source dataset
uspto-grants-1987_06
Patent number
US04670420

Reaction notes

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