Bromotrimethylsilane → HCID 66673169, compound

HRID 1269406Notes

Reaction equation

HRID 1269406 reaction equation
C(OC([NH:8][C@:9]([CH3:40])([CH2:20][CH2:21][C:22]1[N:23]([CH3:39])[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]([CH3:40])([CH2:20][CH2:21][C:22]1[N:23]([CH3:39])[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 86596706HCID 86596706, compound

Product 1

HCID 66673169HCID 66673169, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl (3R)-3-t-butoxycarbonylamino-3-methyl-5-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]pentylphosphonate (114.0 mg, 0.20 mmol) obtained in Example (44c) in dichloromethane (2.0 ml) was added bromotrimethylsilane (0.26 ml, 1.97 mmol), and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 5 hours. After stirring, the reaction mixture was evaporated in vacuo, and the residue was diluted with aqueous ethanol and then 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 (52.0 mg, yield: 63%).

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-b9f2a992d1824353bfef6480675b3c88
Source dataset
uspto-grants-2007_04
Patent number
US07199150B2

Reaction notes

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