Hydrochloric Acid → 2-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-yloxy]-2-methyl-propionic acid

HRID 1498498Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-yloxy]-2-methyl-propionic acid ethyl ester (103 mg, 0.24 mmol) in methanol (5 mL) was added water (0.5 mL) and lithium hydroxide monohydrate (19 mg, 0.48 mmol). The reaction mixture was heated at 50° C. for 16 h then HCl (1N, aq.) added until pH˜4. The reaction mixture was concentrated in vacuo to give 2-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-yloxy]-2-methyl-propionic acid as a yellow solid. LCMS: RT=2.88 min, [M+H]+=399

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-016b70d7d165459cb0704d7d3409fd14
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198918B2

Reaction notes

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