Hydrochloric Acid → HCID 86754910, compound

HRID 379447Notes

Reaction equation

HRID 379447 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[N:20](CC3OC(CO)=CC=3)[C:19]3[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[O:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl.[CH2:40](OCC)[CH3:41]>>[OH:33][CH2:38][C:37]1[O:36][C:35]([CH2:34][CH:9]2[CH2:10][CH:11]([C:14]([C:16]3[NH:17][C:18]4[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=4[N:20]=3)=[O:15])[CH2:12][CH2:13][NH:8]2)=[CH:41][CH:40]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-Dioxane2×HCID 21697585HCID 21697585, compound

Product 1

HCID 86754910HCID 86754910, compound

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine (5 mmol) and dioxane (25 mL). Slowly add a solution of hydrochloric acid in dioxane (1.25 mL, 4 M, 5 mmol). After 45 minutes, add diethyl ether and evaporate in vacuo to give a residue. Partition the residue between dichloromethane and saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract with brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. customevaporate in vacuo
  2. customto give a residue
  3. customPartition the residue between dichloromethane and saturated aqueous sodium bicarbonate solution
  4. customSeparate the organic layer
  5. extractionextract with brine
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-1c8c1300cc5e48d5ad94f372a9d86bb1
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Reaction notes

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