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

HRID 629945
Notes
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Reaction equation

HRID 629945 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 86667771(E)-ethyl 2-(4-(2-(3-(diethoxyphosphoryl)-3,3-difluoropropoxy)ethoxy)-2-methoxybenzylidene)-3-oxobutanoate

Product 1

HCID 178476979HCID 178476979, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962Water
Solvent
HCID 8857Ethyl AcetateSolvent

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

  1. temperatureto cool to room temperature
  2. customThe resulting mixture was transferred to a separatory funnel
  3. washwashed with EtOAc three times
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customthe volatiles were removed in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes