Pyridine → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl)-D-glucitol

HRID 1009889ノート

反応式

HRID 1009889 の反応式
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].N1C=CC=CC=1.[NH2:20][CH2:21][CH2:22][C:23]1[CH:83]=[CH:82][C:26]([CH2:27][C:28]2[C:29]([CH3:81])=[CH:30][C:31]([O:73][CH2:74][C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=3)=[C:32]([C@@H:34]3[O:63][C@H:62]([CH2:64][O:65][CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)[C@@H:53]([O:54][CH2:55][C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C@H:44]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@H:35]3[O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:33]=2)=[CH:25][CH:24]=1.[NH2:84][C:85]([CH3:89])([CH3:88])[CH2:86][OH:87]>O.CS(C)=O.C(Cl)(Cl)Cl>[CH2:37]([O:36][C@@H:35]1[C@@H:44]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C@H:53]([O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C@@H:62]([CH2:64][O:65][CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[O:63][C@H:34]1[C:32]1[CH:33]=[C:28]([CH2:27][C:26]2[CH:82]=[CH:83][C:23]([CH2:22][CH2:21][NH:20][C:2]([NH:84][C:85]([CH3:89])([CH3:88])[CH2:86][OH:87])=[O:3])=[CH:24][CH:25]=2)[C:29]([CH3:81])=[CH:30][C:31]=1[O:73][CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

参加物

8

反応物 4

HCID 1049PyridineHCID 118072-Amino-2-methyl-1-propanolHCID 821294-Nitrophenyl chloroformateHCID 67303921(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[5-[4-(2-aminoethyl)benzyl]-2-(benzyloxy)-4-methylphenyl]-D-glucitol

生成物 1

HCID 86638449(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl)-D-glucitol収率 65%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒3 回

実験手順

To a chloroform solution (3 mL) of 4-nitrophenyl chloroformate (0.177 g, 0.879 mmol) and pyridine (0.071 mL, 0.88 mmol), which was cooled in ice, was added dropwise a chloroform solution (3 mL) of (1S)-1-[5-[4-(2-aminoethyl)benzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol (0.250 g, 0.293 mmol), and the mixture was stirred for 20 minutes at room temperature. After that, a chloroform solution (3 mL) of 2-amino-2-methyl-1-propanol (0.209 g, 2.344 mmol) and dimethyl sulfoxide (3 mL) were added thereto, and the mixture was stirred overnight at the same temperature. To the reaction solution was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine (3 times), and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure to obtain a residue. Thus obtained residue was purified with NH type silica gel column chromatography (chloroform) to obtain the title compound (0.184 g, 65%) as a pale yellow oily compound.

後処理

  1. stirringthe mixture was stirred overnight at the same temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine (3 times)
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure
  7. customto obtain a residue
  8. customThus obtained residue was purified with NH type silica gel column chromatography (chloroform)

出典と根拠

ORDレコード
ord-bca74ef6b0ba4612883ca67f2e298548
出典データセット
uspto-grants-2011_07
特許番号
US07973012B2

反応ノート

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