Trimethylsilyl iodide → HCID 86753212, compound

HRID 399428Notes

Reaction equation

HRID 399428 reaction equation
[O:1]=[C:2]1[N:6]2[CH:7]=[C:8]([C:11]([NH:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[O:12])[CH:9]=[CH:10][C:5]2=[N:4][N:3]1[CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24](C(OCC2C=CC=CC=2)=O)[CH2:23][CH2:22]1.I[Si](C)(C)C>C(#N)C>[O:1]=[C:2]1[N:6]2[CH:7]=[C:8]([C:11]([NH:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[O:12])[CH:9]=[CH:10][C:5]2=[N:4][N:3]1[CH2:19][CH2:20][CH:21]1[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86753213HCID 86753213, compound

Product 1

HCID 86753212HCID 86753212, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-6 (64 mg, 0.129 mmole) in acetonitrile (15 ml) at 0° was treated with iodotrimethylsilane (107.0 mg, 0.533 mmole) and the reaction stirred 0.5 h. The reaction was quenched into water, extracted with diethyl ether and chromatographed on silica using EtOH/NH4 OH/H2O (10/1/1) to give upon concentration a white foam. Crystallization from ethanol gave 1-7 as a white solid, mp 267°-269°. ##STR40## 2(S)-[6-Butylsulfonyl)amino]-3[[[2,3-dihydro-3-oxo-2-[2-(N-CBZ-Piperidin-4-yl)ethyl]-1,2,4 -triazolo[4,3-a]Pyridin-6-yl]carbonyl[amino Propionic acid (1-8)

Workup

  1. customThe reaction was quenched into water
  2. extractionextracted with diethyl ether
  3. customchromatographed on silica
  4. customto give upon concentration a white foam
  5. customCrystallization from ethanol

Sources & evidence

ORD record
ord-c2e3f205989e41dea7a23368a9342215
Source dataset
uspto-grants-1998_10
Patent number
US05821241

Reaction notes

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