Triethylsilane → HCID 9973488, compound

HRID 1707327Notes

Reaction equation

HRID 1707327 reaction equation
[CH2:1]([NH:9][C:10](=[O:48])[C@H:11]([C@H:44]([CH2:46][CH3:47])[CH3:45])[NH:12][CH2:13][C@@H:14]([NH:36]C(OC(C)(C)C)=O)[CH2:15][S:16]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:1]([NH:9][C:10](=[O:48])[C@H:11]([C@H:44]([CH2:46][CH3:47])[CH3:45])[NH:12][CH2:13][C@@H:14]([NH2:36])[CH2:15][SH:16])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 10055192HCID 10055192, compound

Product 1

HCID 9973488HCID 9973488, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The product of Step D (0.09 g, 0.14 mmol) was dissolved in 4 mL of 25% trifluoroacetic acid (TFA) in CH2Cl2 at ambient temperature, triethylsilane (0.089 mL, 0.56 mmol) was added and the solution was stirred for 3 h. The reaction mixture was concentrated and partitioned between EtOAc and aqueous saturated NaHCO3 solution. The organic layer was washed with brine and dried (Na2SO4). Filtration, concentration and trituration with hexane provided 0.02 g (44%) of the title compound, mp 69°-73° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between EtOAc and aqueous saturated NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration, concentration and trituration with hexane

Sources & evidence

ORD record
ord-bd09be1ffd1a47eba1795ac91e3524b6
Source dataset
uspto-grants-1994_10
Patent number
US05352705

Reaction notes

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