Ethanol → HCID 131734894, compound

HRID 920844Notes

Reaction equation

HRID 920844 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:15][N:14]2[N:16]=[C:17]([I:24])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]2[C:12](=O)[NH:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)C>C1COCC1>[Si:1]([O:8][CH2:9][CH:10]1[CH2:15][N:14]2[N:16]=[C:17]([I:24])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]2[CH2:12][NH:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 702EthanolHCID 131734895HCID 131734895, compound

Product 1

HCID 131734894HCID 131734894, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of Intermediate 351C (1.2 g, 2.503 mmol) in THF (120 ml) was added neat borane dimethylsulfide complex (0.713 mL, 7.51 mmol) dropwise and the resulting solution was heated at 40° C. for 36 h. The reaction mixture was cooled to room temperature and ethanol (10 mL) was added dropwise. The reaction mixture was stirred at 70° C. for 1 h and concentrated to afford Intermediate 351D as a white semi-solid (1.23 g, 95%), which was taken to the next step without further purification. MS(ES): m/z=466 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4c0af20013044e39b46afa9c4248c36a
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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