Boron tribromide → HCID 59344724, compound

HRID 2426483Notes

Reaction equation

HRID 2426483 reaction equation
C([O:8][CH2:9][C@@H:10]1[N:17]2[C:18](=[O:38])[C:19]([O:36]C)=[C:20]3[C:25]([CH2:24][CH2:23][N:22]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=4)[C:21]3=[O:35])=[C:16]2[C:15](=[O:39])[N:14]([CH3:40])[CH2:13][CH2:12][CH2:11]1)C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[F:33])[CH2:26][N:22]1[CH2:23][CH2:24][C:25]2[C:20](=[C:19]([OH:36])[C:18](=[O:38])[N:17]3[C@@H:10]([CH2:9][OH:8])[CH2:11][CH2:12][CH2:13][N:14]([CH3:40])[C:15](=[O:39])[C:16]3=2)[C:21]1=[O:35]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66997784(6R)-6-[(benzyloxy)methyl]-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2-methyl-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione

Product 1

HCID 59344724HCID 59344724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6R)-6-[(benzyloxy)methyl]-11-(3-chloro-4-fluorobenzyl)-9-methoxy-2-methyl-3,4,5,6,12,13-hexahydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridine-1,8,10(11H)-trione (167 mg, 0.29 mmol) in dichloromethane (2.9 mL) was cooled to 0° C. and treated with boron tribromide (295 mg, 1.18 mmol). The cooling bath was removed and the mixture stirred at room temperature for 30 minutes. The reaction was quenched by the addition of MeOH followed by 1 N aqueous HCl. The mixture was diluted with dichloromethane and washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was subjected to reverse phase column chromatography on C-18 stationary phase eluted with a 95-5% water-acetonitrile gradient. Collection and concentration of appropriate fractions afforded the title compound.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched by the addition of MeOH
  3. additionThe mixture was diluted with dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. washeluted with a 95-5% water-acetonitrile gradient
  9. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-a2b95bff4f52451396656fbf5c72b182
Source dataset
uspto-grants-2011_06
Patent number
US07968564B2

Reaction notes

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