HCID 57010990, compound → HCID 57313599, compound

HRID 496639Notes

Reaction equation

HRID 496639 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:11]=2[C:12]([NH:14][C@@H:15]([CH2:20][CH2:21][S:22][CH3:23])[C:16]([O:18][CH3:19])=[O:17])=[O:13])=[CH:4][CH:3]=1>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:11]=2[C:12]([NH:14][C@@H:15]([CH2:20][CH2:21][S:22][CH3:23])[C:16]([O:18][CH3:19])=[O:17])=[O:13])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 57010990HCID 57010990, compound

Product 1

HCID 57313599HCID 57313599, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of compound 55 (2 g), stannous chloride dihydrate(4.4 g) and ethyl acetate (150 ml) was stirred and heated at reflux for 2 hours. It was then cooled and treated dropwise with aequeous ammonia(0.880) to pH 9. The white precipitate formed was filtered and washed with more ethyl acetate (150 ml). The filtrate and washings were combined, dried and evaporated to dryness to give an oil which was purified by flash chromatography on silica using ethyl acetate/iso-hexane as eluant to give methyl (2S)-2-{2-[2-(4-fluorophenyl)ethynyl]-4-aminobenzoylamino}-4-methylsulfanylbutyrate as a yellow solid (compound 56) (1.1 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureIt was then cooled
  4. customThe white precipitate formed
  5. filtrationwas filtered
  6. washwashed with more ethyl acetate (150 ml)
  7. customdried
  8. customevaporated to dryness
  9. customto give an oil which
  10. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-ef68591c47dc47b187af5dd1cf3d5a2e
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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