HCID 178449508, compound → HCID 178449509, compound

HRID 903395Notes

Reaction equation

HRID 903395 reaction equation
[N+:1]([N:4]([S:20]([C:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:28]([N:29]([CH3:31])[CH3:30])[C:27]=2[CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C@H:5]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])[CH2:6][CH2:7][CH2:8][NH:9][C:10](=[NH:12])[NH2:11])([O-])=[O:2]>C1(OC)C=CC=CC=1.F>[N:1]#[N:4].[OH2:2].[S:20]([NH:4][C@H:5]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])[CH2:6][CH2:7][CH2:8][NH:9][C:10](=[NH:11])[NH2:12])([C:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[C:28]([N:29]([CH3:30])[CH3:31])[C:27]=2[CH:26]=[CH:25][CH:24]=1)(=[O:21])=[O:22]

Participants

4

Reactant 1

HCID 178449508HCID 178449508, compound

Product 1

HCID 178449509HCID 178449509, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 7519AnisoleSolventHCID 14917Hydrofluoric AcidSolvent

Procedure

A 1.0 gram amount of NG -nitro-N2 -dansyl-N-(n-butyl)-L-argininamide, which was prepared in the same manner as described in Example 26, was dissolved in a mixture of 1 ml of anisole and 2 ml of hydrogen fluoride, and the mixture was stirred for 30 minutes in an ice-bath. The hydrogen fluoride was evaporated in vacuo to afford an oily product, which was washed well with 100 ml of dry ethyl ether to remove the hydrogen fluoride. The thus obtained powdery product was neutralized with a solution of 3 ml of triethylamine in a small amount of water. Then N2 -dansyl-N-(n-butyl)-L-argininamide monohydrate was obtained in 73% yield; mp. 145°-148° C.

Workup

  1. customwas prepared in the same manner
  2. customThe hydrogen fluoride was evaporated in vacuo
  3. customto afford an oily product, which
  4. washwas washed well with 100 ml of dry ethyl ether
  5. customto remove the hydrogen fluoride

Sources & evidence

ORD record
ord-692186f8c7dd4a059e792410865f29f7
Source dataset
uspto-grants-1980_10
Patent number
US04227006

Reaction notes

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