Bromotrimethylsilane → HCID 57935153, compound

HRID 1433765Notes

Reaction equation

HRID 1433765 reaction equation
C[O:2][P:3]([CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[C:19](=[O:20])[N:18]([C@H:21]([C:30](=[O:40])[NH:31][C:32]3[CH:37]=[CH:36][C:35]([I:38])=[CH:34][C:33]=3[F:39])[C@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])[C:17](=[O:41])[NH:16]2)=[CH:11][CH:10]=1)(=[O:6])[O:4]C.Br[Si](C)(C)C>ClCCl>[F:39][C:33]1[CH:34]=[C:35]([I:38])[CH:36]=[CH:37][C:32]=1[NH:31][C:30]([C@@H:21]([N:18]1[C:19](=[O:20])[C@@H:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][P:3](=[O:2])([OH:6])[OH:4])=[CH:14][CH:13]=2)[NH:16][C:17]1=[O:41])[C@H:22]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH3:23])=[O:40]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 57935171HCID 57935171, compound

Product 1

HCID 57935153HCID 57935153, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-{(R)-1-[(1S,2S)-1-(2-fluoro-4-iodo-phenylcarbamoyl)-2-phenyl-propyl]-2,5-dioxo-imidazolidin-4-yl}-phenoxymethyl)-phosphonic acid dimethyl ester (prepared as described in example 63) (79 mg, 0.11 mmol) in dichloromethane (2.0 mL) was added bromotrimethylsilane (0.12 mL, 0.88 mmol) at room temperature. After 4 hours, the reaction was concentrated in vacuo and diluted with water (5 mL). The precipitated solids were filtered and dried to give (4-{(R)-1-[(1S,2S)-1-(2-fluoro-4-iodo-phenylcarbamoyl)-2-phenyl-propyl]-2,5-dioxo-imidazolidin-4-yl}-phenoxymethyl)-phosphonic acid (51 mg, 68%).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additiondiluted with water (5 mL)
  3. filtrationThe precipitated solids were filtered
  4. customdried

Sources & evidence

ORD record
ord-271bcdccd27f402ab4b6c9b00ba2c469
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

Loading…