Hydrochloric Acid → HCID 86754910, compound

HRID 609780Notes

Reaction equation

HRID 609780 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-d09b011d9d8146daaeaef846bac2513e
Source dataset
uspto-grants-1999_12
Patent number
US05998439

Reaction notes

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