tert-Butanol → HCID 25135993, compound

HRID 2355884Notes

Reaction equation

HRID 2355884 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.C([OH:31])(C)(C)C>[Zn]>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:31])[CH2:9]2

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 25136283HCID 25136283, compound

Product 1

HCID 25135993HCID 25135993, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
27.5 °C

Procedure

PyHBr3 (1.28 g, 4.02 mmol) was added in small portions over 30 min to a solution of (R)-2-benzyloxycarbonylamino-3-(1H-indol-5-yl)-propionic acid methyl ester (0.47 g, 1.34 mmol) in t-butanol (10 mL) while the reaction temperature was maintained between 25-30° C. The resulting mixture was stirred at room temperature for 3.5 h. The solvent was removed in vacuo, and the residue was extracted with ethyl acetate (2×). The combined organic phases were washed with brine and dried over sodium sulfate. After filtration, solvents were removed and the residue was azeotropically dried with anhydrous ethanol. The residue was dissolved in glacial acetic acid (10 mL) and zinc powder (0.88 g, 13.4 mmol) was added. The mixture was stirred at room temperature overnight. After the acetic acid was removed in vacuo, the residue was purified by flash chromatography on silica gel using ethyl acetate/hexanes [(1:3) first and then (3:2)] as eluent to afford the title compound as a white solid (41% for 2 steps).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue was extracted with ethyl acetate (2×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration, solvents
  6. customwere removed
  7. dry with materialthe residue was azeotropically dried with anhydrous ethanol
  8. dissolutionThe residue was dissolved in glacial acetic acid (10 mL)
  9. stirringThe mixture was stirred at room temperature overnight
  10. customAfter the acetic acid was removed in vacuo
  11. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ba3812b4826e4f76a1de77ff87a4b8f5
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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