Sodium Hydroxide → HCID 67337738, compound

HRID 1678431Notes

Reaction equation

[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[N:6]=[C:5]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]([O:25]CC)=[O:24])[CH2:18][CH2:17]2)[N:4]=1.[OH-].[Na+]>>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)[N:6]=[C:5]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][CH2:17]2)[N:4]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 86644317HCID 86644317, compound

Product 1

HCID 67337738HCID 67337738, compoundYield 50%

Conditions

Temperature: 60 °C

Procedure

To the solution prepared in step c was added 6 N NaOH (6 mL), and the resulting mixture was heated to 60° C. overnight. The reaction mixture was cooled to room temperature, and purified directly (without concentrating or work up) using reverse-phase HPLC (Phenomenex, 2-15% CH3CN/H2O, 0.1% TFA, 6 min) to afford 0.95 g (50%) of the title compound. MS (ES+): m/e 351.1 [M+H]+.

Workup

temperatureThe reaction mixture was cooled to room temperature
custompurified directly (
concentrationwithout concentrating
customreverse-phase HPLC (Phenomenex, 2-15% CH3CN/H2O, 0.1% TFA, 6 min)

Sources & evidence

ORD record: ord-1104e7a9049c4ae2b2f35b35e2b9505e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008483B2

Reaction notes

Loading…