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Potassium Carbonate → HCID 57079992, compound

HRID 2299620
Notes
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Reaction equation

HRID 2299620 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:44]=[CH:43][C:11]2[CH2:12][CH2:13][CH2:14][CH:15]([N:17]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:18][C@H:19]([O:28][Si:29]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16][C:10]=2[CH:9]=1.Br[CH2:46][F:47].C(=O)([O-])O.[Na+]>C(#N)C.CN(C)C=O>[F:47][CH2:46][O:7][C:8]1[CH:44]=[CH:43][C:11]2[CH2:12][CH2:13][CH2:14][CH:15]([N:17]([C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])[CH2:18][C@H:19]([O:28][Si:29]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:34][CH3:35])[CH2:20][O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:16][C:10]=2[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 61108BromofluoromethaneHCID 516892Sodium BicarbonateHCID 57157362HCID 57157362, compound

Product 1

HCID 57079992HCID 57079992, compound

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, to a suspension of potassium carbonate (76 mg) in a mixture of acetonitrile (5 ml) and N,N-dimethylformamide (2 ml) was added N-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxycarbonylamine (150 mg) at room temperature. After being stirred at the same temperature for 30 minutes, to this one was an excessive amount of bromofluoromethane, and the mixture was stirred for 12 hours. The resulting solution was poured into saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1) to give N-(3-fluoromethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxycarbonylamine (130 mg).

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-4656f41331344820b0720dc735d3cdb8
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06495546B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes