Methanol → HCID 21697585, compound

HRID 609779Notes

Reaction equation

HRID 609779 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[N:20]([CH2:21][C:22]3[O:23][C:24]([CH2:27][O:28][Si](C(C)(C)C)(C)C)=[CH:25][CH:26]=3)[C:19]3[CH:36]=[CH:37][CH:38]=[CH:39][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[F-].[NH4+].O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([C:16]2[N:20]([CH2:21][C:22]3[O:23][C:24]([CH2:27][OH:28])=[CH:25][CH:26]=3)[C:19]3[CH:36]=[CH:37][CH:38]=[CH:39][C:18]=3[N:17]=2)=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25516Ammonium fluorideHCID 21697527HCID 21697527, compound

Product 1

HCID 21697585HCID 21697585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1-(5-(t-butyldimethylsilyloxy)methylfur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine (7 mmol) and methanol (40 mL). Add ammonium fluoride (42 mmol). Heat to reflux. After 20 hours, concentrate in vacuo to give a residue. Combine the residue with water and dichloromethane. Separate the layers and extract the aqueous layer twice with dichloromethane. Combine the organic layers and dry over Na2SO4, filter, and concentrate in vacuo to give 1-(t-butoxycarbonyl)-4-(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine.

Workup

  1. temperatureHeat to reflux
  2. concentrationconcentrate in vacuo
  3. customto give a residue
  4. customSeparate the layers
  5. extractionextract the aqueous layer twice with dichloromethane
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d7237484fe7c47b4b6592e8ffb525423
Source dataset
uspto-grants-1999_12
Patent number
US05998439

Reaction notes

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