Water → HCID 57092673, compound

HRID 130518Notes

Reaction equation

HRID 130518 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7][C@@H:8]([CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O)[C@@H:9]([CH3:13])[CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[N-:27]=[N+:28]=[N-:29].[Na+].O>CS(C)=O>[C:1]([O:5][C:6](=[O:26])[CH2:7][C@@H:8]([CH2:14][N:27]=[N+:28]=[N-:29])[C@@H:9]([CH3:13])[CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 57214598HCID 57214598, compound

Product 1

HCID 57092673HCID 57092673, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of the tosylate 21 (1.19 g, 3.1 mmol) and sodium azide (402 mg, 6.2 mmol) in DMSO (15 mL) was warmed to 60° C. for 2.5 hours. Water (100 mL) was added and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (9: 1 hexane/ethyl acetate) gave the azide 22 (628 mg, 80%) as a colorless oil. 1H NMR (CDCl3) δ 3.4 (dd, 1H, J=12.21 and 6.11 Hz), 3.3 (dd, 1H, J=21.11 and 6.59 Hz), 2.30 (dd, 1H, J=15.14 and 3.66 Hz), 2.25 (m, 1H), 2.05 (dd, 1H, J=15.14 and 9.04 Hz), 1.55 (m, 1H), 1.45 (s, 9H), 1.35 (m, 1H), 0.95 (d, 1H, J=6.59 Hz ), 0.90 (d, 1H, J=6.83 Hz), 0.80 (d, 1H, J=7.08 Hz). MS (m/z): (relative intensity): 228 [M−N2, 35%], 172 [M−N2-tBu, 100%].

Workup

  1. extractionthe solution extracted with ether
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b0ed73e9a0ed483980bf3802c2319f35
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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