Benzyl Alcohol → HCID 178454052, compound

HRID 1984941Notes

Reaction equation

HRID 1984941 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12](C(O)=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:20]([CH2:23]C)CC)C.C1([O:31]P(N=[N+]=[N-])(=O)OC2C=CC=CC=2)C=CC=CC=1.[CH2:44]([OH:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1C=CC=CC=1>[CH2:44]([O:51][C:23](=[O:31])[NH:20][C@H:12]1[CH2:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:14][CH2:13]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 178453971HCID 178453971, compound

Product 1

HCID 178454052HCID 178454052, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of cis-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (50.0 g, 206 mmol) in benzene were added triethylamine (26.9 g, 266 mmol) and phosphorazidic acid diphenyl ester (62.2 g, 226 mmol). The reaction mixture was stirred at 80° C. for 1 hr. Benzyl alcohol (31.4 g, 290 mmol) was added and the mixture was stirred at reflux for 24 hr. The reaction mixture was concentrated and the residue was dissolved in EtOAc and H2O. The organic layer was separated and the aqueous layer was extracted with EtOAc (twice). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (silica gel, 30% EtOAc in hexane) to give cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester (54.1 g, 76%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 24 hr
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in EtOAc
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with EtOAc (twice)
  7. dry with materialThe combined organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography (silica gel, 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-b12ea9c165974b88a3486e0434d09a99
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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