Benzyl Alcohol → (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester

HRID 412412

Reaction equation

HRID 412412 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7]C(O)=O)[C:4](=[O:11])[O:3]1.C([N:15]([CH2:18]C)CC)C.C1([O:26]P(N=[N+]=[N-])(=O)OC2C=CC=CC=2)C=CC=CC=1.[CH2:39]([OH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1>[CH2:39]([O:46][C:18](=[O:26])[NH:15][CH2:7][C@H:5]1[C:4](=[O:11])[O:3][C:2]([CH3:1])([CH3:12])[O:6]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Product 1

HCID 67483545(S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl esterYield 69.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)acetic acid (1 g, 5.7 mmol) and triethylamine (0.66 g, 6.5 mmol) in toluene (20 mL) was added phosphorazidic acid diphenyl ester (1.7 g, 6.2 mmol). The solution was heated to reflux for 1 hour. Benzyl alcohol (0.54 g, 5 mmol) was added and reflux was maintained for additional 6 hours. After cooling, the solution was partitioned between ethyl acetate (2×50 mL) and aqueous sodium hydrogen carbonate (10%, 2×50 mL). The organic layers were collected, dried (sodium sulphate) and the solvent removed by evaporation in vacuo to afford 976 mg of crude (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester as an oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hour
  3. temperaturereflux
  4. temperaturewas maintained for additional 6 hours
  5. temperatureAfter cooling
  6. customthe solution was partitioned between ethyl acetate (2×50 mL) and aqueous sodium hydrogen carbonate (10%, 2×50 mL)
  7. customThe organic layers were collected
  8. dry with materialdried (sodium sulphate)
  9. customthe solvent removed by evaporation in vacuo

Sources & evidence

ORD record
ord-f28c776081874cc496ca29242572d1f3
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Linked notes

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