water acetonitrile CCl4 → HCID 86718377, compound

HRID 1518765Notes

Reaction equation

HRID 1518765 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C@@H:21]([CH3:46])[C@H:22]([N:28]([CH3:45])[C:29](=[O:44])[C@@H:30]([N:32]([CH3:43])[C:33](=[O:42])[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:31])[C:23]1[O:24]C=CC=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:47].C(Cl)(Cl)(Cl)Cl.CC#N>CC#N.O>[CH2:35]([O:34][C:33]([N:32]([CH3:43])[C@@H:30]([CH3:31])[C:29]([N:28]([C@@H:22]([C@H:21]([CH3:46])[CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:23]([OH:24])=[O:47])[CH3:45])=[O:44])=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 2

HCID 22592919water acetonitrile CCl4HCID 86718378HCID 86718378, compound

Product 1

HCID 86718377HCID 86718377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of NalO4 (485.0 mg, 2.30 mmol, 6.0 equiv) in H2O/CCl4/CH3CN (3/2/3, 10.4 mL) was added RuCl3 (26.6 mg, 0.13 mmol, 0.34 equiv) and the mixture was stirred vigorously for 15 minutes. To the mixture was then added a solution of 2.18.1g (242.0 mg, 0.38 mmol) in CH3CN (3 mL). After stirring for 15 minutes, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with saturated aqueous NaHSO3 solution, brine, dried over Na2SO4, and concentrated to give product 2.18.1h (242.0 mg) which was used for the next step without further purification. MS m/z (M+1) 619.4.

Workup

  1. stirringAfter stirring for 15 minutes
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with saturated aqueous NaHSO3 solution, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give product 2.18.1h (242.0 mg) which
  7. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-a9d71d66683d4b88bf5a0b617a9a16a2
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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