Acetic Acid → 17-[2-(2-Isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

HRID 2242460Notes

Reaction equation

C([O:3][C:4]([C:6]12[CH2:23][CH:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[CH:13]1[CH:9]([CH2:10][CH:11]([O:26][C:27]3[C:36]4[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=4)[N:30]=[C:29]([C:39]4[N:40]=[C:41]([NH:44][CH:45]([CH3:47])[CH3:46])[S:42][CH:43]=4)[CH:28]=3)[CH2:12]1)[C:8](=[O:48])[NH:7]2)=[O:5])C.[Li+].[OH-].C(O)(=O)C.C1(C)C=CC=CC=1>C1COCC1.CO.O.C(Cl)(Cl)Cl>[CH:45]([NH:44][C:41]1[S:42][CH:43]=[C:39]([C:29]2[CH:28]=[C:27]([O:26][CH:11]3[CH2:10][CH:9]4[CH:13]([C:14](=[O:25])[N:15]([CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][CH:22]5[C:6]([C:4]([OH:5])=[O:3])([NH:7][C:8]4=[O:48])[CH2:23]5)[CH2:12]3)[C:36]3[C:31](=[CH:32][C:33]([O:37][CH3:38])=[CH:34][CH:35]=3)[N:30]=2)[N:40]=1)([CH3:47])[CH3:46]

Participants

Conditions

Temperature: 60 °C

Procedure

To the solution of the ester 109 (21 mg, 0.031 mmol) in a mixture of THF (0.2 ml) and methanol (0.3 ml) was added solution of LiOH (4 mg, 0.17 mmol) in 0.15 ml water. The resulting mixture was stirred at 60° C. for 3.5 h. After cooling to room temperature, acetic acid was added (30 eq). The mixture was co-evaporated with toluene. The residue was distributed between chloroform and water, the water phase was extracted with chloroform 3 times, the organic phases were combined, dried over sodium sulphate and evaporated which gave 20 mg of pure product (yield 99%).

Workup

temperatureAfter cooling to room temperature
extractionthe water phase was extracted with chloroform 3 times
dry with materialdried over sodium sulphate
customevaporated which

Sources & evidence

ORD record: ord-bbc0852b0e9c44febb41543e2c9496d0
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671032B2

Reaction notes

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