Potassium Carbonate → HCID 86721880, compound

HRID 1049030Notes

Reaction equation

HRID 1049030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Cl:21][C:22]1[CH:43]=[CH:42][C:25]([CH2:26][N:27]([CH2:38][CH:39]([CH3:41])[CH3:40])[S:28]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C@@H:12]([O:37][C:34]2[CH:35]=[CH:36][C:31]([S:28](=[O:29])(=[O:30])[N:27]([CH2:26][C:25]3[CH:42]=[CH:43][C:22]([Cl:21])=[CH:23][CH:24]=3)[CH2:38][CH:39]([CH3:41])[CH3:40])=[CH:32][CH:33]=2)[C@H:10]([OH:11])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylateHCID 86721879HCID 86721879, compound

Product 1

HCID 86721880HCID 86721880, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (354 mg, 1.8 mmol) in EtOH (5 mL) was added K2CO3 (246 mg, 1.8 mmol) and a solution of N-(4-chloro-benzyl)-4-hydroxy-N-isobutyl-benzenesulfonamide (629 mg, 1.78 mmol) in EtOH (5 mL) and the reaction was heated at 95° C. for 16 hours. The reaction was left to cool to room temperature and concentrated. Water and EtOAc were added, extracted, washed with brine, dried with Na2SO4 then concentrated and purified by silica gel column chromatography (0-100% EtOAc in cyclohexane) to give (+/−)trans-4-{4-[(4-chloro-benzyl)-isobutyl-sulfamoyl]-phenoxy}-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (259 mg, 26%). LCMS (m/z, Method A) ES+ 553 [M+1]+.

Workup

  1. waitThe reaction was left
  2. concentrationconcentrated
  3. additionWater and EtOAc were added
  4. extractionextracted
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationthen concentrated
  8. custompurified by silica gel column chromatography (0-100% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-68a6e7969a084e26b4feb1007cb59969
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

Loading…