Water → HCID 59639634, compound

HRID 2249840Notes

Reaction equation

HRID 2249840 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][C:29]([NH:31][CH2:32][CH2:33][O:34]C)=[O:30])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:36].B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][C:29]([NH:31][CH2:32][CH2:33][OH:34])=[O:30])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:36]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 59639571HCID 59639571, compound

Product 1

HCID 59639634HCID 59639634, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a soln of the product of Example 205 (50 mg, 0.1 mmol), in dichloromethane (2 mL) was added 1 M boron tribromide in dichloromethane (0.5 mL, 0.5 mmol). The mixture was stirred at 23° for 2 h, H2O was added, extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated to give the crude material. Recrystallization from dichloromethane and hexane afforded the title product (30 mg, 62%). LC-MS: 484.2 (MH+, m/z), 1.59 (Rt, min).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give the crude material
  5. customRecrystallization from dichloromethane and hexane

Sources & evidence

ORD record
ord-93c0720baf084932bdaf144f729b2492
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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