Trimethylsilyl iodide → HCID 131722099, compound

HRID 366087Notes

Reaction equation

HRID 366087 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([C:32]([NH:34][C@@H:35]([C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)[CH3:36])=[O:33])[NH:16][C:17](=[O:31])[CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(OCC1C=CC=CC=1)=[O:2].C[Si](I)(C)C>CC#N>[NH4+:11].[OH-:2].[C:25]1([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]([NH:16][C@@H:15]([C:32]([NH:34][C@@H:35]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[CH3:36])=[O:33])[CH2:14][CH2:13][CH2:12][NH2:11])=[O:31])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 131722100HCID 131722100, compound

Product 2

HCID 14923Ammonium HydroxideHCID 131722099HCID 131722099, compoundYield 127.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared according to the method described in Example 6(d) above from (R)-N5 -(Cbz)-N2 -(diphenylacetyl)-(R)-N-[1-(1-naphthyl)ethyl]ornithine amide (1.0 g; 1.63 mmol; from step (c) above), trimethylsilyliodide (0.36 g, 1.79 mmol) and CH3CN (60 mL) at 0° C., 3.5 hours reaction time. The resultant heterogeneous solution was submitted to aqueous work up and chromatographed on silica eluting with CH2Cl2 :MeOH:conc. NH4OH (88.5:10:1.5) to afford the sub-title compound as a solid (0.5 g).

Workup

  1. customPrepared
  2. customreaction time
  3. customchromatographed on silica eluting with CH2Cl2

Sources & evidence

ORD record
ord-3ad98b2ecd9f46f4806a9166ee1b32f8
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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