Triethylsilane → HCID 58349438, compound

HRID 2090063Notes

Reaction equation

HRID 2090063 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][C:31]([O:37][CH3:38])=[N:32]3)(O)[C@@H:9]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][C:31]([O:37][CH3:38])=[N:32]3)[C@@H:9]([C:13]2[CH:25]=[CH:24][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 58349500HCID 58349500, compound

Product 1

HCID 58349438HCID 58349438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

The product of step A (85 mg, 0.160 mmol) was dissolved in CH2Cl2 (15 mL) and triethylsilane (0.26 ml, 1.6 mmol) was added. The solution was cooled to −78° C., then BF3 gas was slowly bubbled through the solution until it was saturated (less than one minute, at the time fuming BF3 was observed from a small needle venting from the flask). The mixture was allowed to warm gradually to −20° C. When all starting material was consumed by LC/MS analysis, 1N HCl (aq) was added and the mixture was allowed to warm to room temperature. The mixture was extracted twice with CH2Cl2. The combined organic extracts were washed with water, dried over MgSO4, then concentrated. This afforded the title compound, which was used in the next step without purification: LC1 2.29 min. (M+H) 460.

Workup

  1. customBF3 gas was slowly bubbled through the solution until it
  2. customless than one minute
  3. temperatureto warm gradually to −20° C
  4. customWhen all starting material was consumed by LC/MS analysis, 1N HCl (aq)
  5. additionwas added
  6. temperatureto warm to room temperature
  7. extractionThe mixture was extracted twice with CH2Cl2
  8. washThe combined organic extracts were washed with water
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-edb37ceb0ffa48048c0b9349d66dd43c
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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