Phosphorus pentachloride → HCID 57695533, compound

HRID 2079859Notes

Reaction equation

HRID 2079859 reaction equation
[CH2:1]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([C:34]2[CH:39]=[C:38]([CH:40]([CH3:42])[CH3:41])[CH:37]=[CH:36][C:35]=2[O:43][CH3:44])[C:15]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[Si]([N:55]=[N+:56]=[N-:57])(C)(C)C>ClCCl>[CH2:19]([O:18][C:17]1[CH:16]=[C:15]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]([C:34]2[CH:39]=[C:38]([CH:40]([CH3:42])[CH3:41])[CH:37]=[CH:36][C:35]=2[O:43][CH3:44])=[CH:13][C:12]=1[C:10]1[N:9]([CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:57]=[N:56][N:55]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 78378AzidotrimethylsilaneHCID 57695524HCID 57695524, compound

Product 1

HCID 57695533HCID 57695533, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid phenethyl-amide (193 mg, 0.33 mmole) was dissolved in anhydrous dichloromethane (5 ml), then phosphorus pentachloride (104 mg, 0.5 mmol) was added and the resulting solution was stirred at r.t. for 3 hr. TMSN3 (0.3 ml, neat) was added and the resulting mixture was stirred at r.t. for 3 hr. After quenching the reaction with sodium bicarbonate solution, the mixture was extracted with dichloromethane (3×20 ml). The combined organic were dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give 5-(4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-yl)-1-phenethyl-1H-tetrazole (201 mg, 89%). M.p.: 118-120° C.; 400 MHz 1H NMR (CDCl3, δ: 7.32-7.23 (m, 8H), 7.19-7.07 (m, 8H), 6.92 (s, 1H), 6.90 (s, 1H), 6.87 (d, J=8.0 Hz, 1H), 6.68 (s, 1H), 5.05 (s, 2H), 4.99 (s, 2H), 4.43 (t, J=7.6 Hz, 2H), 3.70 (s, 3H), 3.11 (t, J=7.6 Hz, 2H), 2.92-2.84 (m, 1H), 1.24 (d, J=7.2 Hz, 6H); LCMS: 611 [M+H].

Workup

  1. stirringthe resulting mixture was stirred at r.t. for 3 hr
  2. customAfter quenching
  3. customthe reaction with sodium bicarbonate solution
  4. extractionthe mixture was extracted with dichloromethane (3×20 ml)
  5. dry with materialThe combined organic 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-edf47dab21354b92b70fd099f14c0cd8
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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