Sodium Hydroxide → HCID 66670079, compound

HRID 1014927Notes

Reaction equation

HRID 1014927 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][CH:12]1[CH2:17][C:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[N:20](C(=O)C)[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][CH:12]1[CH2:17][C:18]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66670086HCID 66670086, compound

Product 1

HCID 66670079HCID 66670079, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing 71 (2.11 g, 5.36 mmol) in MeOH (30 mL) at 0° C. was added 1M NaOH (8.1 mL, 8.05 mmol) in a dropwise fashion. After 1 h, TLC analysis revealed complete consumption of 71 [EtOAc, Rf(71)=0.4; Rf(72)=0.2]. The MeOH was removed in vacuo and the residue was dissolved in EtOAc, washed with dilute aqueous HCl, water, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 1.99 g of crude 72 which was used in the next step without further purification.

Workup

  1. customconsumption of 71 [EtOAc, Rf(71)=0.4; Rf(72)=0.2]
  2. customThe MeOH was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with dilute aqueous HCl, water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford 1.99 g of crude 72 which
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-9f349d52a2b04cc48b00f3d433d514b1
Source dataset
uspto-grants-2011_07
Patent number
US07985735B2

Reaction notes

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