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Sodium Bicarbonate → 2-[8-[N-benzyl-N-[(2S)-3-(4-benzyloxyphenoxy)-2-hydroxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide

HRID 2299671
Notes
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Reaction equation

HRID 2299671 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.[CH2:29]([O:36][C:37]1[CH:47]=[CH:46][C:40]([O:41][CH2:42][C@H:43]2[O:45][CH2:44]2)=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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)[CH2:44][C@H:43]([OH:45])[CH2:42][O:41][C:40]1[CH:46]=[CH:47][C:37]([O:36][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:38][CH:39]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2733225Ytterbium triflateHCID 11817709(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxiraneHCID 180072362-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-N-butylacetamide

Product 1

HCID 57028317
2-[8-[N-benzyl-N-[(2S)-3-(4-benzyloxyphenoxy)-2-hydroxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide
Yield 46.2%

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 (388 mg) and (2S)-1-(4-benzyloxyphenoxy)-2,3-epoxypropane (340 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (63 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)-3-(4-benzyloxyphenoxy)-2-hydroxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N-butylacetamide (300 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-8f2350c99b714ebabe625e99f25fa0c2
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