Bromotrimethylsilane → HCID 66673169, compound

HRID 1869669Notes

Reaction equation

HRID 1869669 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 61.8%

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 k).

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-0d9187c60c40468ca42cc1ca85ff055b
Source dataset
uspto-grants-2009_12
Patent number
US07638551B2

Reaction notes

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