Carbonic acid-guanidine (1:1) → HCID 178476979, compound

HRID 629945Notes

Reaction equation

[CH2:1]([O:3][P:4]([C:9]([F:35])([F:34])[CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:31]=[CH:30][C:19](/[CH:20]=[C:21](\[C:27](=O)[CH3:28])/[C:22](OCC)=[O:23])=[C:18]([O:32][CH3:33])[CH:17]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(=O)(O)O.[NH2:40][C:41]([NH2:43])=[NH:42]>CO.O.CCOC(C)=O>[NH2:43][C:41]1[N:42]=[C:22]([OH:23])[C:21]([CH2:20][C:19]2[CH:30]=[CH:31][C:16]([O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:9]([P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:3][CH2:1][CH3:2])([F:35])[F:34])=[CH:17][C:18]=2[O:32][CH3:33])=[C:27]([CH3:28])[N:40]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (E)-ethyl 2-(4-(2-(3-(diethoxyphosphoryl)-3,3-difluoropropoxy)ethoxy)-2-methoxybenzylidene)-3-oxobutanoate (1 equiv.) in MeOH (0.20 M) was added guanidine carbonate (1.1 equiv.) and the reaction mixture was heated to 80° C. for 3 h. At this point the reaction mixture was allowed to cool to room temperature and it was then diluted with water and EtOAc. The resulting mixture was transferred to a separatory funnel and washed with EtOAc three times. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system using a gradient of 0-10% MeOH/DCM to provide the title compound (15%) as a solid.

Workup

temperatureto cool to room temperature
customThe resulting mixture was transferred to a separatory funnel
washwashed with EtOAc three times
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
customthe volatiles were removed in vacuo
customThe resulting residue was purified by a COMBIFLASH™ system

Sources & evidence

ORD record: ord-9b7b628470c649d480e70beccb29b8ad
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315530B2

Reaction notes

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