Acetic Acid → HCID 12015899, compound

HRID 1280816Notes

Reaction equation

HRID 1280816 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([CH2:25][CH3:26])[N:13]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(/N=[N:37]/[C:38]([O:40]CC(Cl)(Cl)Cl)=O)=O)C(Cl)(Cl)Cl.C(O)(=O)C.C[Si]([N:54]=C=O)(C)C>C(OCC)C.C1COCC1.O.[Zn]>[C:1]([O:5][C:6](=[O:27])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([NH:37][C:38]([NH2:54])=[O:40])=[C:12]([CH2:25][CH3:26])[N:13]2[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 70696Trimethylsilyl isocyanateHCID 6183558HCID 6183558, compoundHCID 12015898tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

Product 1

HCID 12015899HCID 12015899, compoundYield 69%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.3 g (6.3 mmol) [[2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid tert-butyl ester and 4.8 g (12.6 mmol) bis(2,2,2-trichloroethyl)azodicarboxylate in diethyl ether was stirred for 24 hours at room temperature. The resulting solid was filtered and vacuum dried. This adduct (1 g, 1.3 mmol) was dissolved in 10 mL of THF and treated with zinc (1 g) and glacial acetic acid (0.5 mL). After stirring for 30 minutes at room temperature an excess of trimethylsilylisocyanate in 1 mL of THF was added stirring was continued at room temperature for 18 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated to dryness to give 0.385 g (69% yield) of the subtitled material. Mass spectrum: 423.

Workup

  1. filtrationThe resulting solid was filtered
  2. customvacuum dried
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-872616fdf8624e3cb302ec74d38e75b9
Source dataset
uspto-grants-2002_09
Patent number
US06451839B1

Reaction notes

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