HCID 131716928, compound → HCID 131716927, compound

HRID 1086284Notes

Reaction equation

HRID 1086284 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][C:14]([CH:16]1[S:20][CH2:19][NH:18][C@@H:17]1[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])=[O:15])[CH2:7]2)([O-])=O>C(O)(=O)C.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][C:14]([CH:16]1[S:20][CH2:19][NH:18][C@@H:17]1[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])=[O:15])[CH2:7]2

Participants

5

Reactant 1

HCID 131716928HCID 131716928, compound

Product 1

HCID 131716927HCID 131716927, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

0.63 g of 1-[3-(5-nitroindan-2-ylacetyl)-L-thioprolyl]pyrrolidine prepared in Example 29 was dissolved in a mixed solution of 9 ml of acetic acid and 6 ml of water. 1.00 g of iron powder was gradually added with stirring. After 1 hour, the iron powder was filtered. The filtrate was alkalinized using 10% sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue obtained was purified by silica gel chromatography to produce 0.34 g of 1-[3-(5-aminoindan-2-ylacetyl)-L-thioprolyl]pyrrolidine as a brownish and oily substance (yield: 59%).

Workup

  1. filtrationthe iron powder was filtered
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe residue obtained
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-803c0d9c015643f89a47e7d404156e8b
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

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