Methanol → HCID 67224698, compound

HRID 1968197Notes

Reaction equation

HRID 1968197 reaction equation
[O:1]=[C:2]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[C@@H:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[N:14](C(OC(C)(C)C)=O)[CH:15]=[C:16]([C:17]([O:19]C)=[O:18])[C:9]=12)[CH2:4][CH3:5].CO.[OH-].[Na+]>C1COCC1>[O:1]=[C:2]([N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)[C@@H:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:9]=12)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58293470HCID 58293470, compound

Product 1

HCID 67224698HCID 67224698, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
53 °C

Procedure

To a 20 mL round bottom flask with a stirrer was added (S)-1-tert-butyl 3-methyl 4-((1-oxo-1-(pyrrolidin-1-yl)butan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (88 mg, 0.198 mmol), MeOH (1 mL) and THF (1 mL). Aqueous NaOH (12N, 1 mL) was added and the reaction mixture was stirred at 53° C. for 16 h. The solvent was removed and the resulting residue was further purified via preparative mass trigger LC-MS (AcCN/H2O, 1-50%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil (6 mg, 9.17%). [M+H] calc'd for C17H22N4O3, 331; found, 331.6.

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was further purified via preparative mass trigger LC-MS (AcCN/H2O, 1-50%)
  3. customThe fractions were collected
  4. concentrationconcentrated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-48793c03059f401b89af58f4babf996d
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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