Triethylamine → HCID 86615474, compound

HRID 1169871Notes

Reaction equation

HRID 1169871 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][C@@H:4]1[O:8][CH2:7][O:6][C@@H:5]1[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].S([N:28]=[N+:29]=[N-])(C1C=CC(C)=CC=1)(=O)=O.CCN(CC)CC>C(#N)C>[CH3:17][C:2]([CH3:1])=[CH:3][C@@H:4]1[O:8][CH2:7][O:6][C@@H:5]1[C:9](=[O:16])[C:10](=[N+:28]=[N-:29])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 86615473HCID 86615473, compound

Product 1

HCID 86615474HCID 86615474, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of keto ester 110 (4.84 g, 20 mmol) in acetonitrile (40 mL) was successively added tosyl azide (4.13 g, 21 mmol) and Et3N (4.4 g, 40 mmol). The resulting reaction mixture was concentrated after stirring for 30 min at room temperature. The diazo derivative was purified by column chromatography (silica gel; hexanes:EtOAc, 95:5) to furnish 112 (3.75 g, 70%) as an oil; IR (neat) 2141, 1713 cm−1; [α]25D=+81.0° (c 2.02, CHCl3); 1H NMR (CDCl3) δ5.77 (ddd, 1 H, J=17.3, 10.1, 7.3 Hz), 5.70 (d, 1 H, J=7.6 Hz), 5.45 (dm, 1 H, J=17.1 Hz), 5.30 (dm, 1 H, J=10.2 Hz), 5.05 (t, 1 H, J=7.5 Hz), 4.36 (q, 2 H, J=7.1 Hz), 1.74 (s, 3 H), 1.51 (s, 3 H), 1.41 (t, 3 H, J=7.1 Hz); FAB MS m/z (relative intensity) 269 (MH+, 86). This compound was used for the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated
  3. customThe diazo derivative was purified by column chromatography (silica gel; hexanes:EtOAc, 95:5)

Sources & evidence

ORD record
ord-2cda366e593947808987e8ee0d1c9e0b
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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