Water → HCID 131728680, compound

HRID 1363388Notes

Reaction equation

HRID 1363388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][C@H:24]1[O:30][C:31](=[O:33])[CH3:32].[N:34]#CBr.O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([O:19][CH3:20])[CH:13]=[C:12]([O:21][CH3:22])[C:11]=2[C@@H:23]1[CH2:28][CH2:27][N:26]([C:29]#[N:34])[CH2:25][C@H:24]1[O:30][C:31](=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 131728679HCID 131728679, compound

Product 1

HCID 131728680HCID 131728680, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To compound of example 126 (2.9 g, 6.15 mmol) in dry CHCl3 (40 mL) at 0° C. was added cyanogen bromide (2.1 g, 19.8 mmol). The reaction mixture was stirred at room temperature for 8 h. It was poured into water (100 mL) and extracted with CHCl3 (3×100 mL). The organic extract was washed with water, dried (anhydrous Na2SO4) and concentrated. The solid residue obtained was purified using a silica gel column and 2% IPA+1% liquor NH3 in CHCl3 as eluant to obtain the title compound.

Workup

  1. extractionextracted with CHCl3 (3×100 mL)
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. customThe solid residue obtained
  7. customwas purified

Sources & evidence

ORD record
ord-f24cb5c2fc5749c3bb7f240c9e652fa8
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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