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Hydrochloric Acid → 4-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoic acid

HRID 1976831
ノート
印刷プレビュー

反応式

HRID 1976831 の反応式
C1(C)C=CC(S(=S)(OCCCC(OC)(OC)OC)=O)=CC=1.[CH3:22][N:23]1[C:28](=[O:29])[C:27]2=[C:30]([S:44][CH2:45][CH2:46][CH2:47][C:48]([O:50]C)=[O:49])[N:31]([CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=3)[CH:32]=[C:26]2[N:25]([CH2:52][CH:53]([CH3:55])[CH3:54])[C:24]1=[O:56].Cl>O1CCCC1.CO>[CH3:22][N:23]1[C:28](=[O:29])[C:27]2=[C:30]([S:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])[N:31]([CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=3)[CH:32]=[C:26]2[N:25]([CH2:52][CH:53]([CH3:54])[CH3:55])[C:24]1=[O:56]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 9913628Methyl 4-[(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1h-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoateHCID 537006924,4,4-Trimethoxybutyl para-toluenethiosulphonate

生成物 1

HCID 154914634-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoic acid収率 33.2%

試薬・触媒・溶媒

1
HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

The compound of Example 2, methyl 4-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]-pyrimidin-5-yl)thio]butanoate (400 mg), was dissolved in 3:1:1 tetrahydrofuran/methanol/1M lithium hydroxide and stirred for 1.5 h before being acidified by dropwise addition of concentrated hydrochloric acid (HCl). The mixture was then extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate (MgSO4) and evaporated to dryness in vacuo. The resultant yellow oil was chromatographed (silica), eluting with 200:10:1 dichloromethane/methanol/glacial acetic acid. The resultant red oil was dissolved in toluene and then evaporated, then similarly with trichloromethane to yield a pink foam. The foam was recrystallised from ethyl acetate/hexane to yield 129 mg of the title compound.

後処理

  1. extractionThe mixture was then extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulphate (MgSO4)
  4. customevaporated to dryness in vacuo
  5. customThe resultant yellow oil was chromatographed (silica)
  6. washeluting with 200:10:1 dichloromethane/methanol/glacial acetic acid
  7. dissolutionThe resultant red oil was dissolved in toluene
  8. customevaporated
  9. customsimilarly with trichloromethane to yield a pink foam
  10. customThe foam was recrystallised from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-164e52b52a9a477b88b493cde3a34255
出典データセット
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06229013B1

反応ノート

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