Sodium Hydroxide → HCID 71205653, compound

HRID 1946534Notes

Reaction equation

HRID 1946534 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[C:14]3[CH:15]([CH2:19][C:20]([O:22]CC4C=CC=CC=4)=[O:21])[CH2:16][CH2:17][CH2:18][C:13]=3[N:12]=[C:11]2[CH:30]([CH3:32])[CH3:31])[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH3:10].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[C:14]3[CH:15]([CH2:19][C:20]([OH:22])=[O:21])[CH2:16][CH2:17][CH2:18][C:13]=3[N:12]=[C:11]2[CH:30]([CH3:32])[CH3:31])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58460189HCID 58460189, compound

Product 1

HCID 71205653HCID 71205653, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 69 (147 mg) was dissolved in Methanol (4 mL). NaOH (2 mL) was added to the stirred reaction mixture as a 3.3 N aqueous soln and the reaction mixture stirred at room temperature. After stirring overnight, LCMS of the reaction mixture demonstrated full consumption of the starting material and the formation of the desired acid product. The reaction mixture was conc in vacuo and taken up in acetonitrile/water. The soln was taken to pH4-5 by the addition of 2 M aqueous HCl and loaded onto an SCX column. After washing with water and acetonitrile, the product was eluted with 2 M ammonia soln in methanol. The washings were conc in vacuo to afford the ammonium salt of the desired product: LC/MS MH+ 361, Rt 2.02 mins (5 min run).

Workup

  1. stirringAfter stirring overnight
  2. customconsumption of the starting material
  3. additionThe soln was taken to pH4-5 by the addition of 2 M aqueous HCl
  4. washAfter washing with water and acetonitrile
  5. washthe product was eluted with 2 M ammonia soln in methanol

Sources & evidence

ORD record
ord-618da8a602f74bd08c0dc162f945173e
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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