Hydrochloric Acid → HCID 178443806, compound

HRID 1383566Notes

Reaction equation

HRID 1383566 reaction equation
[B-](F)(F)(F)F.CN(C(ON1[C:22](=[O:23])[CH:21]2[CH:17]([C@H:18]3[CH:25]=[CH:24][C@@H:20]2[CH2:19]3)C1=O)=[N+](C)C)C.[NH2:26][C@H:27]([C:34]([OH:36])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1.[OH-:37].[Na+].Cl.[OH2:40]>CN(C)C=O.CC(C)=O.C(N(CC)CC)C>[CH2:22]([O:23][C:32]([NH:31][CH2:30][CH2:29][C:28]([NH:26][C@H:27]([C:34]([OH:36])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:40])=[O:37])[CH2:21][CH2:17][CH2:18][CH2:25][CH2:24][CH2:20][CH3:19]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 11810633HCID 11810633, compoundHCID 178419078HCID 178419078, compound

Product 1

HCID 178443806HCID 178443806, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

30 g of N-octyloxycarbonyl-62 -alanine were dissolved in 300 ml of dimethylformamide and 1 molar equivalent of triethylamine. Next, 1 molar equivalent of 2-(5-norbornene-2,3-dicarboximido)-1,1,3,3-tetramethyluronium tetrafluoroborate was added. The mixture was then stirred for 1 hour at a temperature of 25° C. Next, a solution containing 1.2 molar equivalents of histidine and 1.2 molar equivalents of sodium hydroxide in 100 ml of water were added dropwise, while keeping the temperature below 30° C. After stirring for 6 hours, the mixture was neutralized with 1 molar equivalent of 5N hydrochloric acid, followed by 100 ml of water. After stirring for 30 minutes, the mixture was poured into 2 liters of acetone. The white precipitate formed was filtered off and dried. The crude product was dissolved in 10 ml/g of refluxing 96% ethanol. The solution was filtered while hot and the product then crystallized at room temperature. After processing the precipitate, 29.4 g of a white crystalline product were obtained (63% yield).

Workup

  1. additionwere added dropwise
  2. customthe temperature below 30° C
  3. stirringAfter stirring for 6 hours
  4. stirringAfter stirring for 30 minutes
  5. customThe white precipitate formed
  6. filtrationwas filtered off
  7. customdried
  8. dissolutionThe crude product was dissolved in 10 ml/g
  9. temperatureof refluxing 96% ethanol
  10. filtrationThe solution was filtered while hot and the product
  11. customthen crystallized at room temperature

Sources & evidence

ORD record
ord-0a9e52e5d26d494d8f7bb35a044b2818
Source dataset
uspto-grants-2001_07
Patent number
US06255344B1

Reaction notes

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