Methanol → HCID 68635764, compound

HRID 1176602Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:13][CH:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][N:24](C(OCC4C=CC=CC=4)=O)[CH2:23][CH:22]3[O:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]4[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=4[CH:53]=3)=[CH:17][CH:16]=2)[CH2:11]1.CO.[OH-].[K+]>O1CCOCC1.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:11][CH:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH:22]3[O:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]4[O:47][CH2:46][CH2:45][N:44]([CH2:48][CH2:49][CH2:50][O:51][CH3:52])[C:43]=4[CH:53]=3)=[CH:17][CH:16]=2)[CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

0.207 g of benzyl 4-[4-(1-benzothiazol-2-ylazetidin-3-yloxy)phenyl]-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidinecarboxylate is dissolved in 8 ml of dioxane. 8 ml each of methanol and 40% KOH are added and the reaction mixture is stirred in a sealed flask at 100° C. over 5 hours. The reaction mixture is subsequently cooled to room temperature, diluted with 40 ml of water and extracted with ethyl acetate (3×40 ml). The combined organic phases are washed with 40 ml of water, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

Workup

temperatureThe reaction mixture is subsequently cooled to room temperature
extractionextracted with ethyl acetate (3×40 ml)
washThe combined organic phases are washed with 40 ml of water
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-f31cefd0d752492aa3d9ea90bd90f47c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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