Ethanol → HCID 69198568, compound

HRID 2222109Notes

Reaction equation

HRID 2222109 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([C:17]3[O:21][C:20]([P:22]([OH:25])([OH:24])=[O:23])=[C:19]([CH2:26][CH3:27])[C:18]=3[CH2:28][CH3:29])[CH:14]=[C:13]([C:30]([OH:32])=[O:31])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:33][CH2:34]N=C=NCCCN(C)C.C(O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([C:17]3[O:21][C:20]([P:22]([OH:25])([OH:24])=[O:23])=[C:19]([CH2:26][CH3:27])[C:18]=3[CH2:28][CH3:29])[CH:14]=[C:13]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22349225HCID 22349225, compound

Product 1

HCID 69198568HCID 69198568, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-bromophenylcarbamoyl)-3-carboxy-5-(diethyl 2-phosphonofuran-5-yl)benzene (1 mmol), EDCI (2 mmol), DMAP (0.1 mmol) and ethanol (1.5 mmol) in 70 mL of CH2Cl2 were stirred at rt for 14 h. After evaporation the mixture was redissolved in MeOH and slurried with 5 g of DOWEX 50WX8-400 free acid and 5 g of DOWEX 1X8-400 bicarbonate resin for 4 h and then filtered. The filtrate was evaporated to provide 1-(3-bromophenylcarbamoyl)-3-carboethoxy-5-(diethyl 2-phosphonofuran-5-yl)benzene.

Workup

  1. customAfter evaporation the mixture
  2. dissolutionwas redissolved in MeOH
  3. waitslurried with 5 g of DOWEX 50WX8-400 free acid and 5 g of DOWEX 1X8-400 bicarbonate resin for 4 h
  4. filtrationfiltered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-dc168aab8cac41d3b871f59f45e42034
Source dataset
uspto-grants-2008_05
Patent number
US07371739B2

Reaction notes

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