Phosphorus pentachloride → HCID 57695530, compound

HRID 2079854Notes

Reaction equation

HRID 2079854 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:31]2[CH:36]=[C:35]([CH:37]([CH3:39])[CH3:38])[CH:34]=[CH:33][C:32]=2[O:40][CH3:41])[C:12]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[Si]([N:52]=[N+:53]=[N-:54])(C)(C)C>ClCCl>[CH2:16]([O:15][C:14]1[CH:13]=[C:12]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:11]([C:31]2[CH:36]=[C:35]([CH:37]([CH3:39])[CH3:38])[CH:34]=[CH:33][C:32]=2[O:40][CH3:41])=[CH:10][C:9]=1[C:7]1[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[N:54]=[N:53][N:52]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 78378AzidotrimethylsilaneHCID 67103012HCID 67103012, compound

Product 1

HCID 57695530HCID 57695530, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid-(3-methoxypropyl)-amide (183 mg, 0.33 mmole) was dissolved in anhydrous dichloromethane (5 ml), then PCl5 (0.5 mmol) was added and the resulting solution was stirred at r.t. for 3 hr. TMSN3 (0.3 ml, neat, excess) was added and the resulting mixture was stirred at r.t. for 3 hr. After quenching the reaction with NaHCO3 solution, and extracting with dichloromethane (20 ml×3), the combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give product 5-(4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-yl)-1-(3-methoxy-propyl)-1H-tetrazole (166 mg, 87%). M.p.: 102-104° C.; 400 MHz 1H NMR (CDCl3) δ: 7.43 (s, 1H), 7.35-7.13 (m, 12H), 6.87 (d, J=8.0 Hz, 1H), 6.70 (s, 1H), 5.07 (s, 2H), 5.03 (s, 2H), 4.34 (t, J=7.2 Hz, 2H), 3.72 (s, 3H), 3.24 (t, J=6.0 Hz, 2H), 3.16 (s, 3H), 2.93-2.81 (m, 1H), 2.06 (pent, J=6.4 Hz, 2H), 1.23 (d, J=6.9 Hz, 6H); LCMS: 579 [M+H].

Workup

  1. stirringthe resulting mixture was stirred at r.t. for 3 hr
  2. customAfter quenching
  3. customthe reaction with NaHCO3 solution
  4. extractionextracting with dichloromethane (20 ml×3)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-96d51916a0e54027b5ed520d2eca1d66
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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