Methanol → HCID 21697585, compound

HRID 379446Notes

Reaction equation

HRID 379446 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-6295723f0112433199825553f29adcf9
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Reaction notes

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