Bromotrimethylsilane → HCID 67565910, compound

HRID 1729185Notes

Reaction equation

HRID 1729185 reaction equation
C[Si](C)(C)[Br:3].C([O:8][P:9]([CH2:18][C@@H:19]([OH:32])[CH2:20][NH:21][CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=1)[CH3:23])([CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10])C>ClCCl>[BrH:3].[C:30]([C:26]1[CH:25]=[C:24]([CH:22]([NH:21][CH2:20][C@H:19]([OH:32])[CH2:18][P:9]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:8])[OH:10])[CH3:23])[CH:29]=[CH:28][CH:27]=1)#[N:31]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 152822883-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester

Product 1

HCID 67565910HCID 67565910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.97 g of trimethylbromosilane is added to a solution of 0.62 g of 3-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester in 10 ml of absolute dichloromethane. The resulting solution is stirred for 24 hours at room temperature, the volatile portions are removed under reduced pressure and the residue is dissolved in 99.9% methanol. The solution is stirred for 1 hour at room temperature, the solvent is removed and the residue is crystallised from ethanol to give 3-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid hydrobromide having a melting point of 209°-210°.

Workup

  1. customthe volatile portions are removed under reduced pressure
  2. dissolutionthe residue is dissolved in 99.9% methanol
  3. stirringThe solution is stirred for 1 hour at room temperature
  4. customthe solvent is removed
  5. customthe residue is crystallised from ethanol

Sources & evidence

ORD record
ord-7c42296f868441828811549b1df200a2
Source dataset
uspto-grants-1994_07
Patent number
US05332729

Reaction notes

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