Sodium Hydroxide → HCID 136128873, compound

HRID 2076450Notes

Reaction equation

HRID 2076450 reaction equation
[Br:1][C:2]1[C:3]([O:41]S(C2C=CC=CC=2)(=O)=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]([CH2:28][CH2:29][NH:30][C:31](=[O:40])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38]C)=[O:37])[O:13][C:14](=[O:27])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:26])[NH:22][CH2:23][C:24]#[CH:25])[CH:8]=[CH:7]2.[OH-].[Na+]>CO>[Br:1][C:2]1[C:3]([OH:41])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]([CH2:28][CH2:29][NH:30][C:31](=[O:40])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])[O:13][C:14](=[O:27])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:26])[NH:22][CH2:23][C:24]#[CH:25])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59163708HCID 59163708, compound

Product 1

HCID 136128873HCID 136128873, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 14-(8-bromo-7-(phenylsulfonyloxy)quinolin-2-yl)-5,12,18-trioxo-13-oxa-4,11,17-triazatricos-1-yn-23-oate (20 mg, 0.026 mmol) in MeOH (500 uL), were added 0.4 N NaOH (500 uL), and the reaction mixture was stirred for 4 h at room temperature. Methanol was removed in vacuo, and remaining mixture was loaded onto a TOYOPEARL SuperQ-650M packed column pre-washed with 0.2 N NaOH. After washing the column with CH3CN/H2O (1:1) twice, the loaded compound was eluted with AcOH/CH3CN/H2O (5:50:45). After remove the CH3CN in vacuo, the remaining mixture was lyophilized overnight to dryness. The residue was dissolved in MeOH/CH3Cl, transferred to a new vial and evaporated to give a yellow gum (15 mg, 0.024 mmol, 92%) and was used for next step without further purification. MS-ESI (m/z): [M+H]+ calculated for C28H36BrN4O7, 619.2 (79Br) and 621.2 (81Br); found 619.3 (79Br) and 621.3 (81Br).

Workup

  1. customMethanol was removed in vacuo
  2. washpre-washed with 0.2 N NaOH
  3. washAfter washing the column with CH3CN/H2O (1:1) twice
  4. washthe loaded compound was eluted with AcOH/CH3CN/H2O (5:50:45)
  5. customAfter remove the CH3CN in vacuo
  6. waitthe remaining mixture was lyophilized overnight to dryness
  7. dissolutionThe residue was dissolved in MeOH/CH3Cl
  8. customevaporated

Sources & evidence

ORD record
ord-2b3d771c67a547e8adea4958319d4506
Source dataset
uspto-grants-2011_04
Patent number
US07923562B2

Reaction notes

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