Trimethylsilyl isocyanate → HCID 66999381, compound

HRID 560183Notes

Reaction equation

HRID 560183 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11]([NH2:26])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C[Si]([N:31]=[C:32]=[O:33])(C)C>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11]([NH:26][C:32]([NH2:31])=[O:33])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 58172076HCID 58172076, compound

Product 1

HCID 66999381HCID 66999381, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

5-Amino-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (40 mg, 0.11 mmol, 1.0 equiv) was dissolved in 10 mL of methylene chloride and 1 mL of triethylamine. Trimethylsilyl isocyanate was added and the solution was stirred overnight. In the morning the reaction was washed with 10 mL of water and the organic layer was concentrated. The crude residue was purified by flash chromatography on silica (10 g of SiO2) using 0% ethyl acetate in methylene chloride to 100% ethyl acetate graded over 25 min at a flow rate of 15 mL/min-then 100% ethylacetate for another 15 min. The fractions with pure product (TLC) were combined and concentrated to provide 5-ureido-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester as a white solid (41 mg). This material was used without further purification.

Workup

  1. washIn the morning the reaction was washed with 10 mL of water
  2. concentrationthe organic layer was concentrated
  3. customThe crude residue was purified by flash chromatography on silica (10 g of SiO2)
  4. waitgraded over 25 min at a flow rate of 15 mL/min
  5. wait-then 100% ethylacetate for another 15 min
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ab9e31b186f24984b60b3b06d9d8be26
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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