Hexamethyldisilazane → HCID 58482517, compound

HRID 1960143Notes

Reaction equation

HRID 1960143 reaction equation
C([O:4][P:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([C:20]2[NH:24][C:23]3[CH:25]=[C:26]([Cl:41])[C:27]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:31][CH:30]=4)=[CH:28][C:22]=3[N:21]=2)([F:19])[F:18])[CH:12]=1)(=[O:10])[O:6]C(C)C)(C)C.C[Si](N[Si](C)(C)C)(C)C.Br[Si](C)(C)C>C(Cl)Cl>[C:32]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:31]=[CH:30][C:29]([C:27]2[C:26]([Cl:41])=[CH:25][C:23]3[NH:24][C:20]([C:17]([F:19])([F:18])[C:13]4[CH:12]=[C:11]([P:5](=[O:4])([OH:10])[OH:6])[CH:16]=[CH:15][CH:14]=4)=[N:21][C:22]=3[CH:28]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 13838HexamethyldisilazaneHCID 76113BromotrimethylsilaneHCID 86761789HCID 86761789, compound

Product 1

HCID 58482517HCID 58482517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 15-2 (32 mg, 0.054 mmol) in 2 mL CH2Cl2 was added hexamethyldisilizane (0.3 mL), followed by bromo trimethylsilane (71 μL, 0.54 mmol). The reaction was allowed to stir for 18 h at ambient temperature. The organic solvent was removed in vacuo, followed by the addition of H2O (2 mL). The crude product was purified by prepatory HPLC using a 30-80% CH3CN with 0.05% trifluoroacetic acid gradient over 20 min. The pure fractions were combined and lyophilized to give the title compound 15-3. 1H NMR 7.42 (1H, t), 7.50-7.56 (4H, m), 7.65-7.94 (10H, m); LC-MS: m/e 511(M+H)+.

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionfollowed by the addition of H2O (2 mL)
  3. customThe crude product was purified by prepatory HPLC
  4. customover 20 min

Sources & evidence

ORD record
ord-865fe1726c0244c18d59fb7a7ad7169d
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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