Benzyloxycarbonyl-L-proline → 1,2,3,5,10,11a-Hexahydro-10-methyl-11H-pyrrolo[2,1-c] [1,4] benzodiazepin-11-one

HRID 268184

反応式

HRID 268184 の反応式
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)(OCC1C=CC=CC=1)=O.C(OC[C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[NH:30][CH3:31])C1C=CC=CC=1>O1CCCC1>[CH3:31][N:30]1[C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[CH2:1][N:11]2[CH2:18][CH2:17][CH2:16][CH:12]2[C:13]1=[O:15]

参加物

4

反応物 2

HCID 101987Benzyloxycarbonyl-L-prolineHCID 21549880o-(benzyloxymethyl)-N-methylaniline

生成物 1

HCID 545015291,2,3,5,10,11a-Hexahydro-10-methyl-11H-pyrrolo[2,1-c] [1,4] benzodiazepin-11-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2.5 g. of N-carbobenzoxyproline, 1.7 g. of N,N'-carbonyldiimidazole and 25 ml. of tetrahydrofuran is stirred for 1 hour at room temperature and 2.2 g. of o-(benzyloxymethyl)-N-methylaniline is added. The mixture is heated at reflux temperature for 4 hours and concentrated to remove the solvent. The residue is mixed with 200 ml. of ethanol and 2 g. of 10% palladium-on-carbon catalyst and shaken in a Parr hydrogenator under about 3 atmospheres of hydrogen pressure until uptake is complete. The catalyst is filtered off and the mother liquor is concentrated to remove volatile materials. The residue is extracted into methylene chloride. This solution is washed twice with water, dried over magnesium sulfate, and heated at reflux temperature for 6 hours with 5 ml. of thionyl chloride. The reaction mixture is washed twice with sodium carbonate solution, once with water and concentrated. The residue is purified by partition chromatography on a diatomaceous earth column using a heptane/ methyl cellosolve solvent system and 1,2,3,5,10,11a-hexahydro- 10-methyl-11H-pyrrolo[2,1-c] [1,4]benzodiazepin-11-one is obtained.

後処理

  1. additionA mixture of 2.5 g
  2. temperatureThe mixture is heated
  3. temperatureat reflux temperature for 4 hours
  4. concentrationconcentrated
  5. customto remove the solvent
  6. additionThe residue is mixed with 200 ml
  7. filtrationThe catalyst is filtered off
  8. concentrationthe mother liquor is concentrated
  9. customto remove volatile materials
  10. extractionThe residue is extracted into methylene chloride
  11. washThis solution is washed twice with water
  12. dry with materialdried over magnesium sulfate
  13. temperatureheated
  14. temperatureat reflux temperature for 6 hours with 5 ml
  15. washThe reaction mixture is washed twice with sodium carbonate solution, once with water
  16. concentrationconcentrated
  17. customThe residue is purified
  18. customby partition chromatography on a diatomaceous earth column

出典と根拠

ORDレコード
ord-59df9d0335f544c0a735260a6598a18a
出典データセット
uspto-grants-1976_03
特許番号
US03947408

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