Acetic Anhydride → 1-Azido-3-(tosyloxy)propan-2-yl acetate

HRID 1011459Notes

Reaction equation

HRID 1011459 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:18])[CH2:14][N:15]=[N+:16]=[N-:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:19]([O:18][CH:13]([CH2:12][O:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10])[CH2:14][N:15]=[N+:16]=[N-:17])(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 142837971-Azido-2-hydroxy-3-tosyloxypropane

Product 1

HCID 575402081-Azido-3-(tosyloxy)propan-2-yl acetateYield 98.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Azido-2-hydroxypropyl 4-methylbenzenesulfonate 14 (1.83 g, 6.70 mmol) was dissolved in CH2Cl2 (15 mL) and treated with TEA (1.4 mL, 10.00 mmol), a catalytic amount of DMAP and acetic anhydride (0.95 mL, 10.00 mmol) at room temperature. After stirring for 1 hr, silica was added to the reaction mixture, the solvent was evaporated and the residue was purified on silica gel using 50% EtOAc/hexanes as the eluent to afford 2.07 g of 15 (98.8% yield) as a thick, clear, colorless oil. 1H NMR (CDCl3, 400 MHz) δ: 7.79 (d, J=8.4 Hz, 2H), 7.37 (d, J=8.0 Hz, 2H), 5.02-5.07 (m, 1H), 4.09-4.21 (m, 2H), 3.43-3.53 (m, 2H), 2.46 (s, 3H), 2.05 (s, 3H). Mass Spec (lo-res): Calc'd for C12H15N3O5S: 313.07; found: 314.1 (M+H+).

Workup

  1. customat room temperature
  2. additionsilica was added to the reaction mixture
  3. customthe solvent was evaporated
  4. customthe residue was purified on silica gel using 50% EtOAc/hexanes as the eluent

Sources & evidence

ORD record
ord-aed9833e258242c6a7de3d570b2b6700
Source dataset
uspto-grants-2011_07
Patent number
US07977361B2

Reaction notes

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