L-Alanine → HCID 178476535, compound

HRID 1659948Notes

Reaction equation

HRID 1659948 reaction equation
CS(O)(=O)=O.[NH2:6][C@H:7]([C:9]([OH:11])=[O:10])[CH3:8].[NH2:12][C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15].[NH2:20][C@H:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26].[NH2:30][C@H:31]([C:39]([OH:41])=O)[CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:38])[NH2:37].[NH2:42][C@H:43]([C:48]([OH:50])=O)[CH2:44][C:45](=[O:47])[OH:46].C([O-])(=O)C.[NH4+:55]>C(#N)C.C(O)CCC.C(O)(=O)C.N1C=CC=CC=1.O>[C:9]([OH:11])(=[O:10])[CH3:7].[C:17]([OH:19])(=[O:18])[CH3:13].[C:27]([OH:29])(=[O:28])[CH3:21].[NH2:30][C@H:31]([C:39]([NH:20][C@H:21]([C:27]([NH:42][C@H:43]([C:48]([NH:12][C@H:13]([C:17]([NH:6][C@@H:7]([C:9]([NH2:55])=[O:11])[CH3:8])=[O:19])[CH:14]([CH3:16])[CH3:15])=[O:50])[CH2:44][C:45](=[O:47])[OH:46])=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:41])[CH2:32][CH2:33][CH2:34][NH:35][C:36](=[NH:38])[NH2:37]

Participants

10

Reactant 7

HCID 5950L-AlanineHCID 5960L-Aspartic AcidHCID 5962L-LysineHCID 6287L-ValineHCID 6395Methanesulfonic AcidHCID 517165Ammonium AcetateHCID 178418600HCID 178418600, compound

Product 1

HCID 178476535HCID 178476535, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 18475367HCID 18475367, compoundSolvent

Procedure

Amino acid analysis following methane sulfonic acid hydrolysis gives the following ratios: Ala 1.00; Val 1.07; Lys 1.02; Arg 1.02; Asp 1.06. TLC data: Rf =0.17 in 4:1:1:2 (n-butanol-acetic acid-pyridine-water) on silica plates. Rf =0.40 in 4:1:1:2 on cellulose plates. Analysis of the product by high pressure liquid chromatography on a μ Bondapak C18 column (97% 0.1 M ammonium acetate: 3% acetonitrile, pH 4.0) shows the product to be 98% pure.

Workup

  1. customgives the following ratios

Sources & evidence

ORD record
ord-dfba79a1930c4a3bb7bfefaeb3264536
Source dataset
uspto-grants-1981_12
Patent number
US04305852

Reaction notes

Loading…