Sodium Hydroxide → HCID 67224063, compound

HRID 1968205Notes

Reaction equation

HRID 1968205 reaction equation
[CH3:1][CH:2]([CH3:33])[C@@H:3]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[N:19](C(OC(C)(C)C)=O)[CH:20]=[C:21]([C:22]([O:24]C)=[O:23])[C:14]=12)[C:4](=[O:10])[N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[OH-].[Na+]>CO>[CH3:1][CH:2]([CH3:33])[C@@H:3]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[C:21]([C:22]([OH:24])=[O:23])[C:14]=12)[C:4](=[O:10])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58293454HCID 58293454, compound

Product 1

HCID 67224063HCID 67224063, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an 8 mL scintillation vial equipped for stirring was added (R)-1-tert-butyl 3-methyl 4-((3-methyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (134 mg, 0.292 mmol). Aqueous NaOH (12N, 2 mL) and MeOH (1 mL) were added and the solution was stirred at 53° C. for 48 h. The reaction mixture was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil.

Workup

  1. customTo an 8 mL scintillation vial equipped
  2. stirringthe solution was stirred at 53° C. for 48 h
  3. customThe reaction mixture was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-90%)
  4. customThe fractions were collected
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9e6a9cc277ed4335a615a65fc6cd6cb5
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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