Trimethylsilyl iodide → HCID 21886219, compound

HRID 723132Notes

Reaction equation

HRID 723132 reaction equation
C(OC([NH:8][C:9](=[NH:46])[C:10]1[S:14][C:13]([S:15][CH3:16])=[C:12]([S:17]([C:20]2[CH:21]=[C:22]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=3[NH:33][C:34](=[O:45])[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][P:41](=[O:44])([OH:43])[OH:42])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:11]=1)=O)(C)(C)C.C[Si](I)(C)C>C(Cl)Cl>[C:9]([C:10]1[S:14][C:13]([S:15][CH3:16])=[C:12]([S:17]([C:20]2[CH:21]=[C:22]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=3[NH:33][C:34](=[O:45])[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][P:41](=[O:42])([OH:43])[OH:44])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:11]=1)(=[NH:8])[NH2:46]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 1458576785-[[3-methyl-2-[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]phenyl]carbamoylamino]pentylphosphonic acid

Product 1

HCID 21886219HCID 21886219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

[5-(3-{3′-[5-(tert-Butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-ureido)-pentyl]-phosphonic acid (0.058 g, 0.076 mmol), trimethylsilyl iodide (0.162 g, 0.756 mmol) and DCM [5 mL] were added to a flask and heated to 40° C. for 10 minutes. The reaction was removed from the heat bath and allowed to stir at room temperature for 1 hour. H2O [56 μL] was added to this solution and stirred for 1 hour. The reaction was concentrated in vacuo. MeOH [2 mL] and 20 wt. % HCl (aq.) [84 μL] were added to the concentrate and allowed to stir at room temperature for 18 hours. Reaction was concentrated in vacuo followed by reverse-phase HPLC [acetonitrile/water (0.01% TFA)] to yield the title compound. ESI-MS (m/z): Calcd. for C25H31N4O6PS3: 611.71 (M+H); found 611.0.

Workup

  1. customThe reaction was removed from the heat bath
  2. additionH2O [56 μL] was added to this solution
  3. stirringstirred for 1 hour
  4. concentrationThe reaction was concentrated in vacuo
  5. additionMeOH [2 mL] and 20 wt. % HCl (aq.) [84 μL] were added to the
  6. concentrationconcentrate
  7. stirringto stir at room temperature for 18 hours
  8. customReaction
  9. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-e8939d98ec5e4072be55b5170cff8a7e
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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