Hydrochloric Acid → HCID 178501458, compound

HRID 1833527Notes

Reaction equation

HRID 1833527 reaction equation
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([S:15]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:17])=[O:16])=[CH:12]2)=[CH:7][CH:6]=1.[ClH:30].[CH3:31]O>>[N:1]#[N:2].[ClH:30].[CH3:31][O:28][C:27](=[O:29])[C@H:19]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26])[NH:18][S:15]([C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[CH:12]=1)(=[O:16])=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178487531HCID 178487531, compound

Product 1

HCID 178501458HCID 178501458, compoundYield 95%

Procedure

A suspension of 1.0 gram of N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginine in 15 ml of anhydrous methanol was saturated with dry hydrogen chloride for one hour. The reaction mixture was refluxed for an additional one hour. After cooling, the reaction mixture was concentrated in vacuo. The residue was triturated with cold ethyl ether to give a crystalline product. After crystallization from methanolethyl ether, N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginine methyl ester hydrochloride was obtained in 95% yield; mp. 115° - 118° C.

Workup

  1. temperatureThe reaction mixture was refluxed for an additional one hour
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe residue was triturated with cold ethyl ether
  5. customto give a crystalline product
  6. customAfter crystallization from methanolethyl ether

Sources & evidence

ORD record
ord-20da4f7d63d2458a805b4a5248a8baea
Source dataset
uspto-grants-1978_01
Patent number
US04066759

Reaction notes

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