Ammonium Chloride → HCID 59132589, compound

HRID 1169856Notes

Reaction equation

HRID 1169856 reaction equation
[F-].[Cs+].[OH:3][C@@H:4]([C@H:30]1[C@@H:34]([CH2:35][OH:36])[O:33][C:32]([CH3:38])([CH3:37])[O:31]1)[C:5]1[N:9]([S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[C:8]([C:16]([O:18][Si](C(C)C)(C(C)C)C(C)C)=[CH2:17])=[N:7][C:6]=1[CH3:29].[NH4+].[Cl-]>C(O)C>[C:16]([C:8]1[N:9]([S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[C:5]([C@@H:4]([OH:3])[C@H:30]2[C@@H:34]([CH2:35][OH:36])[O:33][C:32]([CH3:37])([CH3:38])[O:31]2)=[C:6]([CH3:29])[N:7]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 25953Cesium fluorideHCID 59132590HCID 59132590, compound

Product 1

HCID 59132589HCID 59132589, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Cesium fluoride (315 mg, 2.08 mmol) was added to a solution of 5-((R)-hydroxy((4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-N,N,4-trimethyl-2-(1-(triisopropylsilyloxy)vinyl)-1H-imidazole-1-sulfonamide (567 mg, 1.04 mmol) in ethanol (10 ml) and warmed to 65° C. After 1 hour, the reaction was cooled to room temperature and treated with saturated aqueous NH4Cl (1 ml), then concentrated. The crude product was purified by flash chromatography over silica gel (5% methanol:dichloromethane eluent) to provide 2-acetyl-5-((R)-hydroxy((4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-N,N,4-trimethyl-1H-imidazole-1-sulfonamide (380 mg, 94% yield) as a white foam: M+1=392.1.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography over silica gel (5% methanol:dichloromethane eluent)

Sources & evidence

ORD record
ord-b6c3f44a1b9448e1ac0b578c0798b5a3
Source dataset
uspto-grants-2010_11
Patent number
US07825150B2

Reaction notes

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