HCID 70239023, compound → HCID 70243273, compound

HRID 1531797Notes

Reaction equation

HRID 1531797 reaction equation
[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C@@H:15]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41]C)[CH:36]=2)[C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[CH2:21][N:20]([CH2:25][C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([OH:31])=[O:30])[CH2:19]3)[C@@H:10]([CH3:43])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>B(Br)(Br)Br>[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C@@H:15]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([OH:41])[CH:36]=2)[C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[CH2:21][N:20]([CH2:25][C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([OH:31])=[O:30])[CH2:19]3)[C@@H:10]([CH3:43])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 70239023HCID 70239023, compound

Product 1

HCID 70243273HCID 70243273, compound

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

Boron tribromide (800 ml of 1N solution in dichloromethane) was added to a stirred solution of the compound of Example 98 (106 mg). The resulting white precipitate was stirred at room temperature for 2 hours. The reaction was quenched with methanolic ammonium hydroxide (1:1 v/v) and evaporated to dryness in vacuo. The residue was purified by column chromatography over silica gel (dichloromethane:methanol:ammonium hydroxide; 84:14:2) to afford the title compound, 36.5 mg.

Workup

  1. customThe reaction was quenched with methanolic ammonium hydroxide (1:1 v/v)
  2. customevaporated to dryness in vacuo
  3. customThe residue was purified by column chromatography over silica gel (dichloromethane:methanol:ammonium hydroxide; 84:14:2)

Sources & evidence

ORD record
ord-310f1129c1c04dae89014562f419b5ae
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

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