Pyridine → HCID 13922619, compound

HRID 986314Notes

Reaction equation

HRID 986314 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][C:14]([NH:16][C@H:17]([C:37]([OH:39])=[O:38])[CH2:18][S:19][S:20][CH2:21][C@H:22]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[C:23]([OH:25])=[O:24])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:40](O)([CH3:43])([CH3:42])[CH3:41].Cl[CH:46](Cl)C.N1[CH:54]=[CH:53][CH:52]=CC=1>>[C:40]([O:24][C:23](=[O:25])[C@@H:22]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])[CH2:21][S:20][S:19][CH2:18][C@H:17]([NH:16][C:14]([O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[C:37]([O:39][C:53]([CH3:52])([CH3:54])[CH3:46])=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 5

HCID 1049PyridineHCID 63651,1-DichloroethaneHCID 6386tert-ButanolHCID 24813Phosphorus oxychlorideHCID 3859726968-11-2

Product 1

HCID 13922619HCID 13922619, compound

Procedure

28 g of phosphorous oxychloride are added to a mixture of 76.2 g of N,N'-dibenzyloxycarbonyl-L-cystine (Chem. Ber., 65 , 1196 (1932)), 89 g of tert-butanol, 95 g of pyridine and 800 ml of dichloroethane at -3° to 2° C. under stirring. The mixture is stirred at the same temperature for 1 hour and at room temperature for 2 hours. The reaction mixture is poured into ice-water, and the organic layer is washed with sodium bicarbonate and water, successively. The organic layer is dried and then evaporated to remove the solvent. The residue is purified by silica gel column chromatography ( solvent; chloroform:isopropyl ether=3:7 ) and recrystallized from a mixture of isopropyl ether and n-hexane. 40.2 g of N,N'-dibenzyloxycarbonyl-L-cystine di-tert-butyl ester are obtained.

Workup

  1. stirringThe mixture is stirred at the same temperature for 1 hour and at room temperature for 2 hours
  2. washthe organic layer is washed with sodium bicarbonate and water
  3. customThe organic layer is dried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography ( solvent; chloroform:isopropyl ether=3:7 )
  7. customrecrystallized from a mixture of isopropyl ether and n-hexane

Sources & evidence

ORD record
ord-f56e216358ed47a39e7cb05106cc3fa8
Source dataset
uspto-grants-1987_12
Patent number
US04711878

Reaction notes

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