HCID 86718370, compound → HCID 86718371, compound

HRID 1518763Notes

Reaction equation

HRID 1518763 reaction equation
[O:1]1C=CC=[C:2]1[C@@H:6]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:7]([CH3:15])[CH2:8][O:9][C@H:10]1[CH2:14][CH2:13][O:12][CH2:11]1.CC[O:27]C(C)=O.CCCCCCC.O>>[C:19]([O:18][C:17]([N:16]([CH3:24])[C@@H:6]([C@H:7]([CH3:15])[CH2:8][O:9][C@H:10]1[CH2:14][CH2:13][O:12][CH2:11]1)[C:2]([OH:1])=[O:27])=[O:23])([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 86718370HCID 86718370, compoundHCID 86718372HCID 86718372, compound

Product 1

HCID 86718371HCID 86718371, compoundYield 73%

Procedure

A flask was charged with 2.16b (50 mg, 0.15 mmol), NalO4 (189 mg, 0.88 mmol, 6 equiv.) and EtOAc/heptane/water (1.5 mL/0.5 mL/2 mL). With vigorous stirring, RuCl3 (6 mg, 0.03 mmol, 0.2 equiv) was added and the resulting mixture was stirred at room temperature for 1 hour. The reaction was quenched by addition of saturated aqueous NaHSO3 solution and the mixture was extracted with EtOAc. The combined organic layers was washed with saturated aqueous NaHSO3 solution, brine, dried over Na2SO4 and concentrated to give product 2.16c (34 mg, 73% yield). MS (m/z): 318 [M+1].

Workup

  1. customThe reaction was quenched by addition of saturated aqueous NaHSO3 solution
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layers was washed with saturated aqueous NaHSO3 solution, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-614cacce51fc471994ec5cf56eee7420
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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