Trimethylsilyl iodide → HCID 178439830, compound

HRID 46149Notes

Reaction equation

HRID 46149 reaction equation
C([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[S:17][C:18]([CH:23]([CH3:25])[CH3:24])([CH3:22])[C:19](=[O:21])[N:20]=1)C1C=CC=CC=1.I[Si](C)(C)C>C(Cl)Cl>[OH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[S:17][C:18]([CH:23]([CH3:25])[CH3:24])([CH3:22])[C:19](=[O:21])[N:20]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 178439829HCID 178439829, compound

Product 1

HCID 178439830HCID 178439830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A 5 mL vial was charged with 2-((1S,2S)-2-(benzyloxy)cyclohexylamino)-5-isopropyl-5-methylthiazol-4(5H)-one (0.100 g, 0.28 mmol) and 1 mL of DCM. To this was added iodotrimethylsilane (0.22 g, 1.1 mmol). The vial was sealed and heated at 65° C. for 36 h. The reaction was concentrated and purified by column chromatography (2% to 7% MeOH/DCM) to give 2-((1S,2S)-2-hydroxycyclohexylamino)-5-isopropyl-5-methylthiazol-4(5H)-one as a yellow solid

Workup

  1. customThe vial was sealed
  2. concentrationThe reaction was concentrated
  3. custompurified by column chromatography (2% to 7% MeOH/DCM)

Sources & evidence

ORD record
ord-117633cd925b4ad782388613026d325d
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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