Dichloromethane → HCID 67148262, compound

HRID 2426311Notes

Reaction equation

HRID 2426311 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-e083262a19d34f07a0458e06950aa905
Source dataset
uspto-grants-2011_06
Patent number
US07968560B2

Reaction notes

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