Tetrahydrofuran → HCID 57722319、化合物

HRID 1986534

反応式

HRID 1986534 の反応式
[NH2:1][CH:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][N:4]([CH3:13])[C:3]1=[O:14].[CH2:15]([CH:17]([CH2:21]CCC)[C:18]([O-])=O)C.[Na+].[CH2:26]([OH:40])[C@@H:27]([OH:39])[C@@H:28]([OH:38])[C@H:29]([OH:37])[C@@H:30]([OH:36])[C@@H:31](O)[C:32](O)=O.ClCCl.[CH3:44]O.[CH2:46]1[CH2:50]OC[CH2:47]1>C(Cl)Cl.C(OCC)(=O)C>[CH3:15][C:17]([CH3:21])([CH3:18])/[CH:32]=[CH:31]/[C@H:30]1[O:36][C:46]([CH3:50])([CH3:47])[O:38][C@@H:28]([C@@H:27]([O:39][CH3:44])[C:26]([NH:1][CH:2]2[CH2:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[CH2:5][N:4]([CH3:13])[C:3]2=[O:14])=[O:40])[C@H:29]1[OH:37]

参加物

8

反応物 5

HCID 8028TetrahydrofuranHCID 25588D-glycero-D-gulo-heptonic acidHCID 21226129Dichloromethane methanolHCID 23672331Sodium 2-ethylhexanoateHCID 57722303HCID 57722303、化合物2 回

生成物 1

HCID 57722319HCID 57722319、化合物収率 59%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 25 mg (0.13 mmol) of product 3, 22 mg (0.13 mmol) of sodium 2-ethylhexanoate and 25 mg (0.088 mmol) of lactone 4 (which may be prepared according to the procedures described in J. Med. Chem, 2001, 44, 3692-3699, starting with the γ-lactone of α-glucoheptonic acid, and the content of which is incorporated herein by reference) in 2 ml of THF are stirred at room temperature under nitrogen. The reaction is continued until the amine 3 has disappeared (about 92 hours), the presence of which is monitored by TLC (90/10 v/v dichloromethane/methanol). After addition of 20 ml of ethyl acetate, the organic phase is washed with 20 ml of saturated aqueous NaCl solution, dried over magnesium sulfate and filtered, and the solvents are then evaporated off under reduced pressure. The residue is purified by chromatography on silica gel, eluting with a 97.5/2.5 v/v dichloromethane/methanol mixture to give a resin. This resin is dissolved in 20 ml of CH2Cl2, washed with 15 ml of 1N NaOH, 15 ml of saturated NaCl solution, dried over MgSO4, filtered and evaporated under reduced pressure to give 24 mg (59%) of the expected product 5 in the form of a resin (2 diastereoisomers).

後処理

  1. custommay be prepared
  2. custom(about 92 hours)
  3. washthe organic phase is washed with 20 ml of saturated aqueous NaCl solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvents are then evaporated off under reduced pressure
  7. customThe residue is purified by chromatography on silica gel
  8. washeluting with a 97.5/2.5 v/v dichloromethane/methanol mixture
  9. customto give a resin
  10. washwashed with 15 ml of 1N NaOH, 15 ml of saturated NaCl solution
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-703a44381c4f4bf796dde6349679c1e5
出典データセット
uspto-grants-2009_06
特許番号
US07550453B2

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