Sodium Hydroxide → HCID 68312906, compound

HRID 1530422Notes

Reaction equation

HRID 1530422 reaction equation
C[O:2][C:3](=[O:31])[C:4]([O:7][C:8]1[CH:30]=[CH:29][C:11]2[C:12]3[N:16]([CH2:17][CH2:18][O:19][C:10]=2[CH:9]=1)[CH:15]=[C:14]([C:20]1[N:21]([CH:26]([CH3:28])[CH3:27])[N:22]=[C:23]([CH3:25])[N:24]=1)[N:13]=3)([CH3:6])[CH3:5].[OH-].[Na+]>CO>[CH:26]([N:21]1[C:20]([C:14]2[N:13]=[C:12]3[N:16]([CH2:17][CH2:18][O:19][C:10]4[CH:9]=[C:8]([O:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:31])=[O:2])[CH:30]=[CH:29][C:11]=43)[CH:15]=2)=[N:24][C:23]([CH3:25])=[N:22]1)([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68312961HCID 68312961, compound

Product 1

HCID 68312906HCID 68312906, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methylpropionic acid methyl ester (39.2 mg, 0.0922 mmol) in MeOH (1.5 mL) was added 1M NaOH (0.46 mL) and the mixture was heated at 100° C. for 1 h using microwave irradiation. After cooling to RT, the organic solvent was removed in vacuo and the pH of the resulting mixture was adjusted to 8 by addition of 1M HCl. The mixture was then subjected to column chromatography (C18, gradient 25-40% MeOH in H2O followed by C18, gradient 1-20% MeOH in H2O) affording 2-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methylpropionic acid (38 mg, quantitative). LCMS: RT 2.82 min [M+H]+ 412.0

Workup

  1. custommicrowave irradiation
  2. temperatureAfter cooling to RT
  3. customthe organic solvent was removed in vacuo
  4. additionthe pH of the resulting mixture was adjusted to 8 by addition of 1M HCl

Sources & evidence

ORD record
ord-16d101d383214f3988b03ffc76367b68
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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