Hydrochloric Acid → HCID 178443806, compound

HRID 411959Notes

Reaction equation

HRID 411959 reaction equation
[CH2:1]([O:9][C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[B-](F)(F)(F)F.CN(C(ON1C(=O)C2C([C@H]3C=C[C@@H]2C3)C1=O)=[N+](C)C)C.[NH2:43][C@H:44]([C:51]([OH:53])=[O:52])[CH2:45][C:46]1[N:50]=[CH:49][NH:48][CH:47]=1.[OH-].[Na+].Cl>CN(C)C=O.O.CC(C)=O.C(N(CC)CC)C>[CH2:1]([O:9][C:10]([NH:12][CH2:13][CH2:14][C:15]([NH:43][C@H:44]([C:51]([OH:53])=[O:52])[CH2:45][C:46]1[N:50]=[CH:49][NH:48][CH:47]=1)=[O:17])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11096866HCID 11096866, compoundHCID 11810633HCID 11810633, compoundHCID 178419078HCID 178419078, compound

Product 1

HCID 178443806HCID 178443806, compoundYield 63%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
250 °C

Procedure

30 g of N-octyloxycarbonyl-β-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 250° 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-d066212d4a474289a0f83265b12131af
Source dataset
uspto-grants-2003_05
Patent number
US06562789B2

Reaction notes

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