Bromotrimethylsilane → HCID 66672910, compound

HRID 562619Notes

Reaction equation

HRID 562619 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 (0.255 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-8aad33a4215244f48aa266524db378da
Source dataset
uspto-grants-2011_11
Patent number
US08067396B2

Reaction notes

Loading…