Water → HCID 54215524, compound

HRID 1723555Notes

Reaction equation

HRID 1723555 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[CH:18][N:19]([CH3:21])[CH3:20])[C:10]2=[O:22])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[CH:18][N:19]([CH3:20])[CH3:21])[C:10]2=[O:22])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 54370108HCID 54370108, compound

Product 1

HCID 54215524HCID 54215524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen, a solution of title product of Example C1 (0.468 g, 1.59 mmoles) in 5 ml CH2Cl2 was cooled to -78°. Boron tribromide (0.45 ml, 4.77 mmoles) was added. After stirring 20 minutes at -78°, the reaction mixture was allowed to warm to room temperature, stirred 2 hours, diluted with 25 ml. of water and then 20 ml CH2Cl2, stirred 15 minutes, and the pH adjusted to 6-7 with saturated NaHCO3. The aqueous layer was separated and extracted 2×25 ml CH2Cl2. The three organic layers were combined, dried over MgSO4, and concentrated to solids in vacuo, 0.402 g. Recrystallization from CH2Cl2 /hexane gave purified title product, 0.320 g, m.p. 200°-203°.

Workup

  1. stirringstirred 2 hours
  2. additiondiluted with 25 ml
  3. customThe aqueous layer was separated
  4. extractionextracted 2×25 ml CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to solids in vacuo, 0.402 g
  7. customRecrystallization from CH2Cl2 /hexane
  8. customgave
  9. custompurified title product, 0.320 g, m.p. 200°-203°

Sources & evidence

ORD record
ord-b7328f90f0f34129820cbe73f24c2672
Source dataset
uspto-grants-1989_08
Patent number
US04861880

Reaction notes

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