Benzyl Alcohol → HCID 178454052, compound

HRID 2389715Notes

Reaction equation

HRID 2389715 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(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1(C)C=CC=CC=1>[CH2:42]([O:49][C:23](=[O:32])[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:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178453971HCID 178453971, compound

Product 1

HCID 178454052HCID 178454052, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

To BOC amino acid (293) (255 mg, 1.05 mmol) and triethylamine (0.58 mL, 4.2 mmol) in toluene (3 mL) at 45° C. was added dropwise diphenyl phosphoryl azide (0.23 ml, 1.15 mmol). Benzyl alcohol (0.16 mL, 1.58 mmol) was then added and the reaction heated at 55° C. for 4 h. The reaction was cooled to RT then washed with H2O, 1M KHSO4, and saturated sodium bicarbonate solution. The organic layer was dried (Na2SO4), filtered and reduced in vacuo to give the title compound.

Workup

  1. temperatureThe reaction was cooled to RT
  2. washthen washed with H2O, 1M KHSO4, and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d618f0e7a6c6465e887e3e43afa0ddef
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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