Hydrochloric Acid → HCID 70563003, compound

HRID 2071283Notes

Reaction equation

HRID 2071283 reaction equation
C(OC([NH:8][C@H:9]([C:22]([NH:24][CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35](=[O:43])[C:36]1[CH:41]=[C:40]([Br:42])[CH:39]=[CH:38][N:37]=1)=[O:27])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:44].C(OCC)C>O1CCOCC1>[ClH:44].[ClH:44].[ClH:44].[NH2:8][C@H:9]([C:22]([NH:24][CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35](=[O:43])[C:36]1[CH:41]=[C:40]([Br:42])[CH:39]=[CH:38][N:37]=1)=[O:27])=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86734479HCID 86734479, compound

Product 1

HCID 70563003HCID 70563003, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.0 g of (Nα,Nε -ditertbutoxycarbonyl-L-lysyl)-N-(4-bromo-2-picolinoylphenyl)glycinamide was stirred for 1 hour in a solution of hydrogen chloride in dioxan (4-M). Diethyl ether was added and the solid which separated was filtered off, washed with diethyl ether and dried. The solid was dissolved in methanol and precipitated with ethyl acetate. The precipitate was dissolved in 20 ml of water and, after extraction with chloroform, the aqueous solution was lyophilised to yield 0.7 g (88%) of L-lysyl-N-(4-bromo-2-picolinoylphenyl)glycinamide trihydrochloride 1.5 H2O; [α]D20 = +20.1° (c = 1 in water).

Workup

  1. customthe solid which separated
  2. filtrationwas filtered off
  3. washwashed with diethyl ether
  4. customdried
  5. dissolutionThe solid was dissolved in methanol
  6. customprecipitated with ethyl acetate
  7. dissolutionThe precipitate was dissolved in 20 ml of water
  8. extractionafter extraction with chloroform

Sources & evidence

ORD record
ord-ed58f4de43884d3488d9b23f0d5e285c
Source dataset
uspto-grants-1977_09
Patent number
US04046751

Reaction notes

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