Benzyl Alcohol → HCID 67491122, compound

HRID 571953Notes

Reaction equation

HRID 571953 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[C:25]([O:29][C:30]([NH:32][C@@H:33]1[CH2:38]CC[C@H:35](C(O)=O)[CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C@H:6]1([NH:3][C:4](=[O:15])[O:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:7][CH2:35][CH2:34][C@@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:38]1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2755995rel-(1R,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclohexanecarboxylic acid

Product 1

HCID 67491122HCID 67491122, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (1.8 mL, 12.9 mmol) and diphenylphosphoryl azide (2.0 mL, 9.27 mmol) were added to a stirred solution of cis-3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (2.0 g, 8.22 mmol) in toluene (50 mL), and the resulting mixture was stirred at rt for 3 h. Benzyl alcohol (1.70 mL, 16.4 mmol) was added, and the mixture was heated to 100° C. After 12 h, the reaction mixture was cooled to rt, diluted with EtOAc, and the resulting mixture was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0-30% EtOAc/hexanes as eluent) to afford the title compound i-1a. m/z (ES) 371 (M+Na)+

Workup

  1. temperaturethe mixture was heated to 100° C
  2. waitAfter 12 h
  3. temperaturethe reaction mixture was cooled to rt
  4. washthe resulting mixture was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0-30% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-52d1315c05e64c4f9329851e4db61ded
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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