HCID 11503270, compound → HCID 11695677, compound

HRID 558026Notes

Reaction equation

HRID 558026 reaction equation
[C:1]([O:4][C@H:5]1[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:12]([CH2:18][O:19][Si](C(C)(C)C)(C)C)[O:11][C@H:7]([S:8][CH2:9][CH3:10])[C@H:6]1[N:27]=[N+:28]=[N-:29])(=[O:3])[CH3:2]>C1COCC1>[C:1]([O:4][C@H:5]1[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:12]([CH2:18][OH:19])[O:11][C@H:7]([S:8][CH2:9][CH3:10])[C@H:6]1[N:27]=[N+:28]=[N-:29])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 11503270HCID 11503270, compound

Product 1

HCID 11695677HCID 11695677, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To compound 23 (305 mg, 0.68 mmol) dissolved in THF (6 mL), TREAT-HF (0.55 ml, 3.38 mmol) was added. The mixture was stirred at rt overnight. Concentration and chromatography (10:1→0:1 toluene-EtOAc) gave 35 (171 mg, 0.51 mmol, 75%); 13C NMR δ 14.7 (SCH2CH3), 20.6, 20.8 (CH3CO), 25.4 (SCH2CH3), 61.3, 63.0, 66.6, 71.1, 71.3 (C-2-6), 82.2 (C-1), 170.0, 170.6 (CH3CO); 1H NMR δ 1.26-1.30 (t, 3H), 2.05 (s, 3H), 2.08 (s, 3H), 2.32 (s, 1H), 2.56-2.68 (m, 2H), 3.58-3.67 (m, 2H), 4.09-4.14 (m, 2H), 5.24-5.35 (m, 3H).

Workup

  1. additionTREAT-HF (0.55 ml, 3.38 mmol) was added
  2. concentrationConcentration and chromatography (10:1→0:1 toluene-EtOAc)

Sources & evidence

ORD record
ord-e4373b2409704832bbcf17482dc80cc1
Source dataset
uspto-grants-2011_11
Patent number
US08062641B2

Reaction notes

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