Bromotrimethylsilane → HCID 66672910, compound

HRID 422917Notes

Reaction equation

HRID 422917 reaction equation
C(OC([NH:8][C@:9]([CH3:39])([CH2:20][CH2:21][C:22]1[O:23][C:24]([C:27](=[O:38])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:25][CH:26]=1)[CH2:10][CH2:11][P:12](=[O:19])([O:16]CC)[O:13]CC)=O)(C)(C)C.Br[Si](C)(C)C>ClCCl>[NH2:8][C@:9]([CH3:39])([CH2:20][CH2:21][C:22]1[O:23][C:24]([C:27](=[O:38])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:25][CH:26]=1)[CH2:10][CH2:11][P:12](=[O:13])([OH:16])[OH:19]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86596704HCID 86596704, compound

Product 1

HCID 66672910HCID 66672910, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl (3R)-3-t-butoxycarbonylamino-3-methyl-5-[5-(5-phenylpentanoyl)furan-2-yl]pentylphosphonate (108.2 mg, 0.19 mmol) obtained in Example (29d) in dichloromethane (1.9 ml) was added bromotrimethylsilane (0.2.55 ml, 1.93 mmol), and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 4 hours. After stirring, the reaction mixture was evaporated in vacuo, and the residue was diluted with aqueous ethanol, and then the resulting mixture was adjusted to pH 4 with aqueous ammonia and acetic acid. The crystals precipitated were collected by filtration, washed successively with water and ethanol and dried to afford the title compound (51.4 mg, yield: 66%).

Workup

  1. stirringAfter stirring
  2. customthe reaction mixture was evaporated in vacuo
  3. additionthe residue was diluted with aqueous ethanol
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed successively with water and ethanol
  7. customdried

Sources & evidence

ORD record
ord-04e541cf7c4b49f2a998a7ce9799832f
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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