HCID 21316320, compound → HCID 23002836, compound

HRID 1658911Notes

Reaction equation

HRID 1658911 reaction equation
O=[C:2]1[CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][C:13](=O)[N:12]2[CH2:21][CH2:22][S:23][CH2:24][CH2:25][S:26][CH2:27][CH2:28][N:3]1[CH2:4][CH2:5][S:6][CH2:7][CH2:8][S:9][CH2:10][CH2:11]2.[H]1[BH2][H][BH2]1>O1CCCC1>[N:3]12[CH2:4][CH2:5][S:6][CH2:7][CH2:8][S:9][CH2:10][CH2:11][N:12]([CH2:21][CH2:22][S:23][CH2:24][CH2:25][S:26][CH2:27][CH2:28]1)[CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:2]2

Participants

3

Reactant 1

HCID 21316320HCID 21316320, compound

Product 1

HCID 23002836HCID 23002836, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.6 g. of the bicyclic diamide obtained in Example 34 in 10 ml. tetrahydrofuran is slowly added to 10 ml. of the freshly prepared B2H6 solution (1.5 M) under nitrogen atmosphere and at a temperature of 0°C. The mixture is refluxed for two hours. The excess reagent is destroyed by adding 5 ml. of water and the solution is evaporated on a rotatory evaporator under vacuum. The solid residue is treated with 50 ml. 6 N hydrochloric acid under reflux for two hours. The mixture is evaporated to dryness under vacuum on a rotatory evaporator. The residue is treated with a solution of tetraethylammonium hydroxide until a basic reaction is obtained. The mixture containing a precipitate, is extracted several times with chloroform. The solutions are filtered through alumina and evaporated to dryness leaving the title compound as a crystalline residue.

Workup

  1. customat a temperature of 0°C
  2. temperatureThe mixture is refluxed for two hours
  3. customThe excess reagent is destroyed
  4. additionby adding 5 ml
  5. customof water and the solution is evaporated on a rotatory evaporator under vacuum
  6. additionThe solid residue is treated with 50 ml
  7. temperature6 N hydrochloric acid under reflux for two hours
  8. customThe mixture is evaporated to dryness under vacuum on a rotatory evaporator
  9. additionThe residue is treated with a solution of tetraethylammonium hydroxide until a basic reaction
  10. customis obtained
  11. additionThe mixture containing a precipitate
  12. extractionis extracted several times with chloroform
  13. filtrationThe solutions are filtered through alumina
  14. customevaporated to dryness

Sources & evidence

ORD record
ord-a73f296b28ee450b8ede6455348b4829
Source dataset
uspto-grants-1976_06
Patent number
US03966766

Reaction notes

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