Benzyl Alcohol → HCID 86598012, compound

HRID 970062Notes

Reaction equation

HRID 970062 reaction equation
C([CH:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])(O)=O.Cl[C:28]([O:30][CH3:31])=[O:29].[N-:32]=[N+]=[N-].[Na+].C(O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1.O.CCOC(C)=O>[CH2:31]([O:30][C:28]([NH:32][CH:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:5][CH2:6][P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])=[O:29])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 6586Methyl chloroformateHCID 33557Sodium AzideHCID 85863446HCID 85863446, compound

Product 1

HCID 86598012HCID 86598012, compoundYield 56.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 0.62 g (1.6 mmol) of (±)-diethyl 3-(carboxy)pentadecylphosphonate (from Example 27, Step B) in 5 mL of THF at 0° C. was treated with 0.27 mL (1.9 mmol) of TEA and 0.23 mL (1.9 mmol) of methyl chloroformate. The resulting mixture was stirred cold for 30 min, then treated with a solution of 0.51 g (7.9 mmol) of sodium azide in 3 mL of water. The resulting mixture was stirred for 2 h at 0° C. The reaction was diluted with 50 mL of EtOAc, washed with 50 mL of 2 N HCl, 50 mL of sat'd NaCl, dried and concentrated. The residue was dissolved in 5 mL of toluene, benzyl alcohol (0.33 mL, 3.2 mmol) was added and the solution was heated to 85° C. for 3 h. The reaction was cooled and directly purified by silica gel chromatography using 7:3 v/v hexane/acetone as the eluant to afford 0.45 g of the title compound: ESI-MS 498.3 (M+H).

Workup

  1. stirringThe resulting mixture was stirred for 2 h at 0° C
  2. washwashed with 50 mL of 2 N HCl, 50 mL of sat'd NaCl
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 5 mL of toluene
  6. temperatureThe reaction was cooled
  7. customdirectly purified by silica gel chromatography

Sources & evidence

ORD record
ord-c043e41ede174c77b2a931bc4536d5b7
Source dataset
uspto-grants-2007_12
Patent number
US07309721B2

Reaction notes

Loading…