Dichloromethane → HCID 67148262, compound

HRID 1864549Notes

Reaction equation

HRID 1864549 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:11]([O:13][C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:29][C:28]([NH:30][CH3:31])=[N:27][CH:26]=2)=[CH:21][CH:20]=1)[C:15]([O-:17])=[O:16])[CH3:12].Cl[CH2:33]Cl>O>[CH2:11]([O:13][C@@H:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[S:29][C:28]([N:30]([CH3:31])[C:9]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:10])=[N:27][CH:26]=2)=[CH:23][CH:24]=1)[C:15]([O:17][CH3:33])=[O:16])[CH3:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 138341n-Heptyl isocyanateHCID 86606240HCID 86606240, compound

Product 1

HCID 67148262HCID 67148262, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.17 ml (1 mmol) of heptyl isocyanate is added to a solution of 0.17 g (0.5 mmol) of 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoate in 10 ml of dichloromethane. The reaction medium is stirred at room temperature for 20 hours. The reaction medium is diluted with water and then extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 50/50 heptane/ethyl acetate mixture. 0.07 g (30%) of methyl 2(S)-ethoxy-3-{4-[2-(3-heptyl-1-methylureido)thiazol-5-yl]phenyl}propanoate is obtained.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by thin-layer chromatography on silica
  7. washeluted with a 50/50 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-3ca16b39c21e48158ba50cdcbd00b5f7
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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