Formaldehyde → HCID 86603186, compound

HRID 1818960Notes

Reaction equation

HRID 1818960 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[O:12])=[N:7][CH:6]=1.C=O.[C:27]([O-])([O-])=[O:28].[K+].[K+]>CS(C)=O.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:5]1[S:9][C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:15]=2)=[O:12])=[N:7][CH:6]=1)[CH2:27][OH:28]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 86603173HCID 86603173, compound

Product 1

HCID 86603186HCID 86603186, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of {2-[3-(3-trifluoromethyl-phenyl)-ureido]-thiazol-5-yl}-acetic acid methyl ester (4.17 mmol), paraformaldehyde (0.95 equiv.) and K2CO3 (0.95 equiv.) in DMSO (10.0 mL) was heated at 50° C. for 1.5 hours. The reaction was cooled, diluted with EtOAc, washed with water, dried and concentrated to give a residue that was purified by flash column chromatography on silica gel (0 to 6% MeOH in EtOAc) to provide 3-hydroxy-2-{2-[3-(3-trifluoromethyl-phenyl)-ureido]-thiazol-5-yl}-propionic acid methyl ester (compound 73.1).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customto give a residue that
  6. customwas purified by flash column chromatography on silica gel (0 to 6% MeOH in EtOAc)

Sources & evidence

ORD record
ord-845eb9ae972f45a89024cb246503f64c
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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