Methanol → HCID 178501457, compound

HRID 2072183Notes

Reaction equation

HRID 2072183 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]([OH:27])=[O:26])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23])(=[O:15])=[O:14].S(Cl)([Cl:30])=O.[CH3:32]O>>[N:1]#[N:2].[ClH:30].[CH3:32][O:26][C:25](=[O:27])[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]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178514628HCID 178514628, compound

Product 1

HCID 178501457HCID 178501457, compoundYield 90%

Procedure

To an ice-cooled suspension of 1.0 gram of N2 -(2-naphthalenesulfonyl)-L-arginine in 15 ml of methanol 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 2 hours, and was evaporated to dryness (syrup). Treatment of the residual syrup with cold ethyl ether gave crude crystals. After recrystallization from methanol-ethyl ether, colorless N2 -(2-naphthalenesulfonyl)-L-arginine methyl ester hydrochloride was obtained in 90% yield; mp. 183° - 186° C.

Workup

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

Sources & evidence

ORD record
ord-7b823e1580e7414da4bf166e42d10346
Source dataset
uspto-grants-1977_09
Patent number
US04049645

Reaction notes

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