Sodium Bicarbonate → 2-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-(1H-indol-5-yloxy)propyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide

HRID 2299670Notes

Reaction equation

HRID 2299670 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([O:20][CH2:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH:18]=[CH:19][C:13]=2[CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:29]1[C:37]2[C:32](=[CH:33][C:34]([O:38][CH2:39][C@H:40]3[O:42][CH2:41]3)=[CH:35][CH:36]=2)[CH:31]=[CH:30]1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([N:8]([CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([O:20][CH2:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH:18]=[CH:19][C:13]=2[CH2:12][CH2:11][CH2:10]1)[CH2:41][C@H:40]([OH:42])[CH2:39][O:38][C:34]1[CH:33]=[C:32]2[C:37](=[CH:36][CH:35]=1)[NH:29][CH:30]=[CH:31]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2733225Ytterbium triflateHCID 180072362-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-N-butylacetamideHCID 23553465(2S)-1-(1H-indol-5-yloxy)-2,3-epoxypropane

Product 1

HCID 693300382-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-(1H-indol-5-yloxy)propyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamideYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a solution of 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-N-butylacetamide (200 mg) and (2S)-1-(1H-indol-5-yloxy)-2,3-epoxypropane (130 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (33 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford 2-[8-[N-benzyl-N-[(2S)-2-hydroxy-3-(1H-indol-5-yloxy)propyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide (160 mg)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-133d4c4268f6466d9902700eff7f2dfa
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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