Hydrogen Bromide → HCID 59344729, compound

HRID 2426473Notes

Reaction equation

HRID 2426473 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:32]C)[C:10](=[O:31])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[C:16](=[O:30])[C:12]3=2)[C:7]1=[O:34].Br>C(O)(=O)C.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:32])[C:10](=[O:31])[N:11]3[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][C:23]([OH:25])=[O:24])[C:16](=[O:30])[C:12]3=2)[C:7]1=[O:34]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 86644105HCID 86644105, compound

Product 1

HCID 59344729HCID 59344729, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl [11-(3-chloro-4-fluorobenzyl)-9-methoxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-decahydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]acetate (50 mg, 0.09 mmol) and 33% hydrogen bromide in acetic acid (1 mL) in dioxane (1 mL) was stirred at room temperature for 1 hour. The product mixture was 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 lyophilization of appropriate fractions afforded the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. washeluted with a 95-5% water-acetonitrile gradient
  3. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-2d6f79b407b74394878d913e81bb9e30
Source dataset
uspto-grants-2011_06
Patent number
US07968564B2

Reaction notes

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