Hydrochloric Acid → HCID 68515101, compound

HRID 748932Notes

Reaction equation

HRID 748932 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:38][CH3:39])(=[O:37])=[O:36])=[CH:31][CH:30]=1)[CH:7]=[CH:6]2.[ClH:40].C(OCC)C.B(Br)(Br)Br>ClCCl>[ClH:40].[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:16][CH:15]=1)=[C:8]([C:29]1[CH:30]=[CH:31][C:32]([S:35]([NH:38][CH3:39])(=[O:36])=[O:37])=[CH:33][CH:34]=1)[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 59751438HCID 59751438, compound

Product 1

HCID 68515101HCID 68515101, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a round bottom flask place the product of Example 69 (85 mg, 0.146 mmol), dichloromethane (5 mL) and a solution of 1.0 M hydrochloric acid in diethyl ether (0.150 mL, 0.150 mmol). Shake this solution at ambient temperature for 2 minutes and then evaporate it in vacuo. After drying in vacuo, add dichloromethane (6 mL) and place this solution in an ice bath with stirring. Add a solution of 1.0 M boron tribromide in dichloromethane (0.32 mL, 0.32 mmol) and stir the reaction for 2-3 hours, keeping the temperature between 0° C.-10° C. Quench the reaction over saturated aqueous sodium bicarbonate then extract it into ethyl acetate. Wash the combined extracts with saturated aqueous sodium bicarbonate, water and brine; then dry (sodium sulfate) and evaporate in vacuo. Purify the crude solid on a Chromatotron (silica gel; 6%-10% MeOH gradient in CH2Cl2). Dissolve the purified material in methanol (5 mL) and add a solution of 1.0 M hydrochloric acid in diethyl ether (0.30 mL). Shake the resulting solution for two minutes at room temperature then evaporate in vacuo to give 71 mg of the title compound (85%). MS (IS+) m/e 533 (M+1-HCl).

Workup

  1. customevaporate it in vacuo
  2. customAfter drying in vacuo
  3. additionadd dichloromethane (6 mL) and place this solution in an ice bath
  4. stirringstir
  5. customthe reaction for 2-3 hours
  6. custombetween 0° C.-10° C
  7. customQuench
  8. customthe reaction over saturated aqueous sodium bicarbonate
  9. extractionthen extract it into ethyl acetate
  10. washWash the combined extracts with saturated aqueous sodium bicarbonate, water and brine
  11. dry with materialthen dry (sodium sulfate)
  12. customevaporate in vacuo
  13. customPurify the crude solid on a Chromatotron (silica gel; 6%-10% MeOH gradient in CH2Cl2)
  14. dissolutionDissolve the purified material in methanol (5 mL)
  15. additionadd a solution of 1.0 M hydrochloric acid in diethyl ether (0.30 mL)
  16. customShake the resulting solution for two minutes at room temperature then evaporate in vacuo

Sources & evidence

ORD record
ord-264482a8c5b746fda4fef3abf51009ad
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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