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tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hex-5-enoate → tert-butyl (3R)-3-({[(1S)-1-(carboxy)-2,2-dimethylpropyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoate

HRID 1700992
ノート
印刷プレビュー

反応式

HRID 1700992 の反応式
[CH3:1][C:2]([CH3:43])([CH3:42])[C@H:3]([NH:14][C:15]([C@H:17]([CH2:26]/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:31]([CH3:41])[CH:30]=1)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>C(O)C.O.[Pd]>[CH3:1][C:2]([CH3:43])([CH3:42])[C@H:3]([NH:14][C:15]([C@H:17]([CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:31]([CH3:41])[CH:30]=1)[CH2:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])[C:4]([OH:6])=[O:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 59875769tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hex-5-enoate

生成物 1

HCID 59875725tert-butyl (3R)-3-({[(1S)-1-(carboxy)-2,2-dimethylpropyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoate収率 97%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 19096565Water ethanol溶媒

実験手順

A solution of tert-butyl (3R,5E)-3-({[(1S)-2,2-dimethyl-1-(benzyloxycarbonyl)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hex-5-enoate (2.205 g, 3.78 mmol) in ethanol/water=10:1 (44 mL) was hydrogenated over 10% palladium on charcoal at 3 bar and room temperature for 6 h. The mixture was filtered through Arbocel filter aid, washing well with ethanol. The filtrate was concentrated under reduced pressure. The residue was dissolved in toluene and evaporated (three times), dissolved in ether and evaporated (twice), and finally dissolved in ether and precipitated as an oil by the addition of hexane. Removal of the solvent under reduced pressure gave tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-(carboxy)propyl]amino}carbonyl)-6-[3-methyl-(4-phenyl)phenyl]hexanoate (1.817 g, 97%) as a colourless foam, m.p. 51-56° C.

後処理

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. washwashing well with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in toluene
  6. customevaporated (three times)
  7. dissolutiondissolved in ether
  8. customevaporated (twice), and
  9. dissolutionfinally dissolved in ether
  10. customprecipitated as an oil by the addition of hexane
  11. customRemoval of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-fa7abc67527d421dbd4597d9fd01cc37
出典データセット
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06350907B1

反応ノート

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