Water → HCID 71205727, compound

HRID 1946514Notes

Reaction equation

HRID 1946514 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][C:19]([O:21]CC)=[O:20])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:4][CH:3]=1.[OH-].[Na+].O>CO.C(#N)C>[NH3:9].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][C:19]([OH:21])=[O:20])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58460181HCID 58460181, compound

Product 1

HCID 71205727HCID 71205727, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Intermediate 51 (170 mg) was dissolved in 2 ml methanol followed by 4 M equivalent of sodium hydroxide and the mixture stirred at room temperature for 24 hr. The reaction mixture was reduced in vacuo and dissolved in a minimum amount of 1:1 acetonitrile:water. This mixture was passed through an SCX ion exchange column (5 g). The column was washed with 1:1 acetonitrile:water, followed by acetonitrile. The product was eluted with 2M ammonia in methanol and reduced in vacuo. LC/MS MH+ 372, Rt 2.12 mins (5 min run, TFA modifier).

Workup

  1. washThe column was washed with 1:1 acetonitrile
  2. washThe product was eluted with 2M ammonia in methanol
  3. customLC/MS MH+ 372, Rt 2.12 mins (5 min run, TFA modifier)

Sources & evidence

ORD record
ord-e6ba7b5f32b746f3aab390fef8871155
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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