Sodium Hydroxide → HCID 69386115, compound

HRID 916845Notes

Reaction equation

HRID 916845 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC(Cl)(Cl)[C:22]([N:24]=C=O)=[O:23].[OH-].[Na+]>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([NH:16][C:22]([NH2:24])=[O:23])[CH:17]=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76400Trichloroacetyl isocyanateHCID 69385721HCID 69385721, compound

Product 1

HCID 69386115HCID 69386115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)aniline (5.16 g) in dry DCM (50 ml) was treated dropwise with a solution of trichloroacetyl isocyanate (2.36 ml) in dry DCM (6 ml) over 10 min. The reaction mixture was stirred at room temperature for 10 min prior to addition of 2M NaOH (50 ml). The reaction mixture was stirred at 70° C. for 5 h and room temperature for 16 h. The aqueous phase was extracted with DCM and the combined organic layers washed with water and concentrated in vacuo. The residue was purified by chromatography (biotage, EtOAc-Petrol 2:1) to give the title compound. LCMS RT=3.78 min.

Workup

  1. stirringThe reaction mixture was stirred at 70° C. for 5 h and room temperature for 16 h
  2. extractionThe aqueous phase was extracted with DCM
  3. washthe combined organic layers washed with water
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (biotage, EtOAc-Petrol 2:1)

Sources & evidence

ORD record
ord-670b8993fe3b4eb6adadca51e9e70dea
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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