Benzyl Alcohol → HCID 67670349, compound

HRID 1417552Notes

Reaction equation

HRID 1417552 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:33](C(O)=O)[CH2:32][CH2:31][C@@:9]32[O:13][CH2:12][C@H:11]([C:14]2[CH:19]=[C:18]([N:20]4[CH:24]=[CH:23][N:22]=[C:21]4[C:25]([F:28])([F:27])[F:26])[CH:17]=[CH:16][C:15]=2[O:29][CH3:30])[CH2:10]3)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])C=CC=CC=1.C([N:57]([CH:60](C)C)CC)(C)C.[CH2:63]([OH:70])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:63]([O:70][C:60]([NH:57][C@H:33]1[CH2:32][CH2:31][C@:9]2([O:13][CH2:12][C@H:11]([C:14]3[CH:19]=[C:18]([N:20]4[CH:24]=[CH:23][N:22]=[C:21]4[C:25]([F:26])([F:27])[F:28])[CH:17]=[CH:16][C:15]=3[O:29][CH3:30])[CH2:10]2)[C@@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:44])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67672163HCID 67672163, compound

Product 1

HCID 67670349HCID 67670349, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3S,5R,6R,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid (40 mg, 0.079 mmol), diphenylphosphoryl azide (24 mg, 0.08 mmol), and diisopropylethylamine (0.017 mL, 0.095 mmol) in toluene was stirred at RT for 0.5 h, and then heated at 100° C. for 50 min. After addition of benzyl alcohol (0.5 mL), the mixture was heated at 100° C. overnight. Upon cooling to RT, the mixture was taken up in 25 mL of ethyl acetate and washed successively with 15 mL of saturated aqueous sodium bicarbonate and 15 mL of brine. Drying over sodium sulfate and evaporation afforded the crude product, which was purified by column chromatography, eluting with 3-5% ethyl acetate in dichloromethane, to give the title compound (30 mg, 62%) as a light brown syrup. Mass spectrum (NH3/CI): m/z=610.1 (M+1).

Workup

  1. temperatureheated at 100° C. for 50 min
  2. temperaturethe mixture was heated at 100° C. overnight
  3. temperatureUpon cooling to RT
  4. washwashed successively with 15 mL of saturated aqueous sodium bicarbonate and 15 mL of brine
  5. dry with materialDrying over sodium sulfate and evaporation
  6. customafforded the crude product, which
  7. customwas purified by column chromatography
  8. washeluting with 3-5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-7545a134aa56488fad6e2c7d49db0547
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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