4-Methylmorpholine → tert-butyl((R)-1-furan-3-ylmethyl-2-hydroxy-ethyl)-carboxylate

HRID 70110ノート

反応式

HRID 70110 の反応式
N[C@H:2]([CH2:6][C:7]1[CH:11]=[CH:10][O:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(OC(N[C@H]([CH2:24][C:25]1[CH:29]=CO[CH:26]=1)C(O)=O)=O)(C)(C)C.CN1CC[O:34][CH2:33]C1.C(OC(Cl)=O)C(C)C>C(COC)OC>[O:9]1[CH:10]=[CH:11][C:7]([CH2:6][C@@H:2]([C:3]([O:5][C:25]([CH3:29])([CH3:26])[CH3:24])=[O:4])[CH2:33][OH:34])=[CH:8]1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 14797110(R)-2-Amino-3-(furan-3-yl)propanoic acidHCID 66736552(R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid

生成物 1

HCID 66735629tert-butyl((R)-1-furan-3-ylmethyl-2-hydroxy-ethyl)-carboxylate

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
-30 °C

実験手順

Starting from (R)-2-amino-3-furan-3-yl-propionic acid (DE3829451), (R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid is prepared. Under argon 420 mg (R)-2-tert-butoxycarbonylamino-3-furan-3-yl-propionic acid are suspended in 2.5 ml dimethoxyethane suspended. The reaction mixture is cooled to −30° C. 220 μl N-methylmorpholine are added and then 240 μl isobutylchloroformate in 1.5 ml dimethoxyethane is added dropwise. The reaction mixture is allowed to come up to −5° C. and the precipitate is quickly filtered. The filtrate is cooled to −15° C. 100 mg sodium borohydride and a few drops of water are added. The reaction mixture is stirred for 1 hour at ambient temperature and evaporated to dryness. The residue is suspended in ethyl acetate. The reaction mixture is dried and evaporated to dryness. 370 mg of the product are obtained as a solid. Analytical HPLC-MS (method D): RT=1.21 min.

後処理

  1. customis prepared
  2. customto come up to −5° C.
  3. filtrationthe precipitate is quickly filtered
  4. temperatureThe filtrate is cooled to −15° C
  5. addition100 mg sodium borohydride and a few drops of water are added
  6. customevaporated to dryness
  7. customThe reaction mixture is dried
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-9783a9c1ea584defa38d1e4af59bb47e
出典データセット
uspto-grants-2014_09
特許番号
US08822474B2

反応ノート

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