Hydrochloric Acid → HCID 86727121、化合物

HRID 1054484ノート

反応式

HRID 1054484 の反応式
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([C@@H:12]([CH3:17])[C:13]([O:15]C)=[O:14])[CH:7]=[N:6][C:5]=2[N:4]([CH3:18])[C:3]1=[O:19].Cl.OP([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([C@@H:12]([CH3:17])[C:13]([OH:15])=[O:14])[CH:7]=[N:6][C:5]=2[N:4]([CH3:18])[C:3]1=[O:19]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 24450Potassium Phosphate, DibasicHCID 40656551Methyl (S)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanoate2 回

生成物 1

HCID 86727121HCID 86727121、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of methyl(S)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanoate (Intermediate 7, 39 g, 146 mmol) in 1,4-dioxane (400 mL) was added 6N HCl (200 mL). The resulting mixture was refluxed for 3 h, then cooled and concentrated under vacuum (water bath temp: 40-45° C.). Water (35 mL) was added to the residue, and the resulting mixture was then stirred for 0.5 h. The precipitate was collected by filtration, washed with cooled water and ethyl acetate to give the (S)-acid (17.3 g, ee: 99%). The filtrate was carefully neutralized with K2HPO4 solution (aq) to pH 4, extracted with (9:1) CH2Cl2:MeOH mixture (2×), dried over MgSO4, filtered, and concentrated. The residue was purified using silica gel chromatography eluting with CH2Cl2:MeOH (9:1) to give additional (S)-acid (3.2 g, ee: 95%).

後処理

  1. temperatureThe resulting mixture was refluxed for 3 h
  2. temperaturecooled
  3. concentrationconcentrated under vacuum (water bath temp: 40-45° C.)
  4. additionWater (35 mL) was added to the residue
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with cooled water and ethyl acetate
  7. customto give the (S)-acid (17.3 g, ee: 99%)
  8. extractionextracted with (9:1) CH2Cl2
  9. dry with materialMeOH mixture (2×), dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified
  13. washeluting with CH2Cl2:MeOH (9:1)
  14. customto give additional (S)-acid (3.2 g, ee: 95%)

出典と根拠

ORDレコード
ord-bc5d45d3bc4f4812ac2ec38413669a5a
出典データセット
uspto-grants-2016_07
特許番号
US09394308B2

反応ノート

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