Hydrochloric Acid → HCID 20230749, compound

HRID 2290910Notes

Reaction equation

HRID 2290910 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:20][CH:19]3[CH:14]([CH2:15][CH2:16][C:17]4[C:24]([O:25][CH3:26])=[C:23]([O:27][CH3:28])[CH:22]=[CH:21][C:18]=43)[CH2:13]2)=O)=[CH:4][CH:3]=1.B.C1COCC1.[ClH:35]>C1COCC1>[ClH:35].[ClH:35].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:12]2[CH2:20][CH:19]3[CH:14]([CH2:15][CH2:16][C:17]4[C:24]([O:25][CH3:26])=[C:23]([O:27][CH3:28])[CH:22]=[CH:21][C:18]=43)[CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 13746019HCID 13746019, compound

Product 1

HCID 20230749HCID 20230749, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of the compound of example 15 (2.6 g, 6.8 mmole) in 35 mL dry THF was stirred under N2 at room temperature as BH3.THF (1M solution, 26.7 mL) was added. The reaction mixture was stirred at reflux for 21/2 hrs. After cooling to 0° C., 30 mL methanolic HCl was added. The reaction mixture was stirred at reflux for 6 hours and at room temperature for 18 hours. The solution was evaporated (in vacuo) to dryness and water was added. After two neutral Et2O extracts, the aqueous layers were basified with 1N KOH and extracted three times with CH2Cl2. The combined basic extracts were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, evaporated, converted to the HCl salt, and dried (in-vacuo) to obtain a gray foam which was crystallized from Et2O/EtOH to yield 1.71 g white solid (57%); mp 233°-5° C.; M+ 366 .

Workup

  1. additionwas added
  2. temperatureat reflux for 21/2 hrs
  3. stirringThe reaction mixture was stirred
  4. temperatureat reflux for 6 hours and at room temperature for 18 hours
  5. customThe solution was evaporated (in vacuo) to dryness and water
  6. additionwas added
  7. extractionextracted three times with CH2Cl2
  8. washThe combined basic extracts were washed with water, saturated aqueous NaCl
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customdried (in-vacuo)
  13. customto obtain a gray foam which
  14. customwas crystallized from Et2O/EtOH

Sources & evidence

ORD record
ord-445cdc3745014edb977dc2cc753b56ee
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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