Hydrochloric Acid → HCID 70559938, compound

HRID 1834137Notes

Reaction equation

HRID 1834137 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.Cl.C(OCC)C>O1CCOCC1>[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 70559938HCID 70559938, compoundYield 100.3%

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 trichydrochloride 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-41aed99ed66e43feba6aff38a7770b17
Source dataset
uspto-grants-1978_01
Patent number
US04069229

Reaction notes

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