Acetic Acid → HCID 12015899, compound

HRID 397859Notes

Reaction equation

HRID 397859 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 is stirred for 24 hours at room temperature. The resulting solid is filtered and vacuum dried. This adduct (1 g, 1.3 mmol) is 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 is added and stirring is continued at room temperature for 18 hours. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is 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 is filtered
  2. customvacuum dried
  3. additionis added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-90d5e1c0073b4d5f871f6a02e2051c2c
Source dataset
uspto-grants-2003_08
Patent number
US06610728B2

Reaction notes

Loading…