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 886439Notes

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-64e428db4c654fb7bc71462aff77b17e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242104B2

Reaction notes

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