Boron tribromide → HCID 59344724, compound

HRID 2066607Notes

Reaction equation

HRID 2066607 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-napthyridine-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 1N 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-86a6a055c3544812b9673aa6d6dfaf28
Source dataset
uspto-grants-2012_10
Patent number
US08293731B2

Reaction notes

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