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 1800264Notes

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-b78b6b9a378d4bf38c5201444148c3a9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343955B2

Reaction notes

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